


Hell Inc. (Full Story)

by PepperySkin



Category: Supernatural
Genre: Alternate Universe, Biting, Blow Jobs, Cunnilingus, Dirty Talk, Dubious Consent, F/M, Group Sex, M/M, Multi, Rough Sex, Sex over a desk, Voyeurism
Language: English
Status: In-Progress
Published: 2014-04-29
Updated: 2016-04-10
Packaged: 2018-01-21 05:53:15
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 12
Words: 36,921
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1540040
Author URL: https://archiveofourown.org/users/PepperySkin/pseuds/PepperySkin
Summary: <blockquote class="userstuff">
              <p>I really enjoyed this universe so this is an extended version of my original ficlet!</p>
<p>This story is set in an alternate universe where Heaven and Hell are corporations that make magical deals with humans in exchange for souls. Castiel and Crowley are the presidents of their respected companies. Castiel and Dean were once a couple but the time Dean spent in Hell has sparked a new ambition in the young executive and he soon found himself climbing to the top of Hell Inc. It was only a matter of time before Dean grew hungry for a certain demon in an Armani suit . . .</p>
            </blockquote>





	1. Heaven Loses An Angel

**Author's Note:**

> This is like a prequel and sequel to my original drabble. The drabble can still be read as a stand alone, but this is the full extended version. Enjoy! Find me on Tumblr at http://vulcanpride.tumblr.com/ <3 <3 <3

“What do you _mean_ Sam would be a better executive than me?!” Dean huffed and walked over to the liquor cabinet and poured himself a drink. His heart was racing and all of the sudden it felt like the walls were closing in on him.

“Now Dean, calm down –" Castiel began but Dean threw up a hand to silence him.

“DON’T tell me to calm down, Castiel! You know I've been working hard for that promotion _for months!_ And you give it to my brother?!” he asked incredulously.

“I’m sorry, Dean, but Sam has better qualifications than you—" Dean walked up right into Castiel’s personal space and began shouting even louder. Castiel was worried his secretary would hear them despite the thick walls.

“ _Fuck you_! Who was the one who sealed the deal with Hillary Clinton last month, huh?! Who got fucking Donald Trump to sign his soul to us? _Not Sam_! I did all that hard work, not to mention the serious numbers I brought in for the company last year –"

“Yes! And you’ve done wonderfully but Sam has a certain—"

“A certain _what?!”_ Dean screamed back, his face now red with anger and from the liquor. Castiel paused trying to choose his words carefully.

“— _finesse_ about him. You may have had a few good sales last year, Dean, but Sam has brought in more politicians, more people _with power_. And besides, I didn’t want people saying I play favorites because _you’re my lover_!”

“Ohhhh, please! You should be worried that people will think you’re _cheating on me_ with my own brother! You took him to Vegas last month _instead of me_ to close that deal—"

“Dean—"

“You took him to _London_ last spring to seal a deal with the prince—“

“ _Dean_!”

“Who even commented on how you two seemed like a _perfect fucking couple—_ ”

“DEAN PLEASE!” Castiel bellowed. He generally spoke so softly that Dean forgot how loud and authoritative he can be. Slightly out of breath Dean set down his drink on the table, harshly, chipping a piece of the glass in the process. His hands were trembling, he had never been so angry before in his life.

“ _What?”_

“Don’t you see? You have a hard time keeping your emotions in check. You need more experience, more practice! I love you with all of my heart but _Sam_ is the better choice for the executive position! I’m sorry! And I—"

“Yeah well if you love him so much _why don’t you date him instead_.”

“—And I can’t help it if you’re jealous of your own brother! Look at how you’re acting! You should be _happy for him_!”

“ _I am_ happy for him. I’m angry with you, you _fucking twat_!” Castiel narrowed his eyes. The one thing he did not stand for was name calling. They have had countless fights about it before and Dean just never seemed to listen.

“Well maybe we should just take a break. Go get dinner or something. Cool down so we don’t do or say something we regret later.”

“That’s your problem, Castiel. You are constantly telling me what to do. How to act, how to feel—"

“I’m your _boss_ , Dean!”

“Not in closed doors. Not in private. You like to remind me of that every time we’re together, alone, trying to talk about our relationship. _You treat me like a child—_ ”

“ _I wouldn't if you didn't act like one,_ ” Dean was taken aback by how harshly Castiel spoke. They both paused for a beat, taking a few deep breaths, letting that sink in. Castiel wanted this to deescalate. He didn’t mean to hurt Dean but sometimes he can just be so . . . _human._ So emotional. “You wouldn’t be so angry if you just _trusted me_ to make good decisions for the both of us.” Dean was quiet for a moment, looking anywhere but at Castiel.

“Fuck that. You don’t respect me.  _Fuck you_. I’m done with you — with us.” He picked up his coat and started walking to the door. Castiel didn't even try and stop him, just put a hand up to his forehead like he had a headache.

“You don’t mean that, Dean.”

“Yes, _I do_! I’m quitting, I’ll go pack up my things now.”

“Dean, please—" Castiel started again but Dean cut him off.

“Anything at your apartment you can just mail to me. I’ll do the same for you.” Castiel slammed his hands down on his desk, several items falling off in the rattle. It surprised Dean, but not as much as what Castiel said next. In a low, venomous tone, he tried to remind Dean who was in charge one last time.

“ _No one will hire you_. Have you thought about that, Dean?! Everyone knows _you’re mine_ and _no one_ will touch you.”

“There you go treating me like _property_ and like I can’t handle myself. I have _plenty_ of friends in high places.”

“ _Fine_ , Dean. _Go_. I’ll be waiting for you to come crawling back to me once you've realized how much of an idiot you are—"

Dean slammed the door as hard as he could, the walls shaking when he left. Castiel sat down at his desk and put his face in his hands. That didn't go as well as he had hoped.


	2. The King Gets What He Wants

Crowley folded his hands and placed them neatly in his lap while he stared at the beautiful dish before him. Meg Masters was dressed sharply in a black clingy dress with simple pearl earrings and a matching necklace. She had on red lipstick which popped against her snow white skin; her curly brown hair pulled up in a messy bun. Crowley licked his lips pointedly, loving the smirk it brought to her lips.

“What can you tell me about yourself, darling?”

“There’s not much to tell. You know my father?”

“Yes I do. Good man. Great sales pitch. _Be with us or die.”_

“Yes, he was a master during his time. Times have changed, though. Our family’s tactics have changed. If there’s one thing my father taught me to get ahead in life is to take what you want. And I don’t think I need to tell you but _I’m a girl who gets what she wants_.” She walked around Crowley’s desk and sat on his lap. He let her – of course he let her – and she wrapped her arms around his neck as he curiously looked up at her. He made no move to touch her – not yet.

“And what do you want, love?”

She smiled flashing her pretty white teeth and began gently nipping at his jaw line, moving back towards his ear. “Power . . . money . . . my own office . . .” She began loosening his tie with one hand, taking Crowley’s hand in her other and placing it high up on her thigh. Crowley took the invitation and slid his hand up her skirt to her lacy panties. He slipped a finger through the side, feeling that she was already wet, and groaned softly into the night air. Grinning, she stood up and bent over his desk, hiking up her skirt to reveal her voluptuous ass pouring out of the red lace panties. Crowley didn't skip a beat – he stood up behind her, grabbing at her ass. He started grinding up against her from behind and pulled her top down to reveal her perky tits. Massaging them gently they both groaned at the feel of them in his skilled hands. Meg threw an arm over her shoulder around Crowley’s neck and pulled him closer for a deep, wet kiss.

“I want you to fuck me,” she whispered to him. Crowley didn't need to be told twice. He abruptly pushed her down on his desk and pulled down her panties, spreading and squeezing her cheeks, liking the pretty way she moaned when he was rough.

“Oh the things I would do to you,” he growled deeply, admiring the view, before shoving his face into her pussy, drinking her up. She gasped in surprise and spread herself wider, moaning harder when he licked long lines up and down her asshole and cunt. Crowley’s tongue was _amazing._ He fucked her pussy in and out with his tongue until she was so wet she was dripping onto his desk. He flipped her around, surprising her again, before diving right back in and sucking on her clit. Meg threw her head back and grabbed at his hair with one hand, the other reaching up to pinch at her nipples. She moaned loudly, chanting little praises and encouragements and wiggling underneath him. He held her down by grabbing her thighs and licked and sucked until she was nearly screaming at her impending orgasm, coming so hard she knocked several things off his desk. He stood up and watched her come down from the pleasure. Her eyes were dark with lust, a deep blush had spread on her cheeks and chest. Crowley licked his lips and wiped his face with one hand. She was so wet it was even on his _tie_. He unzipped his pants pulling his cock out and unceremoniously thrust inside her wet cunt, slamming into her relentlessly. Her little cries of pleasure filled the room, she wrapped her arms and legs around him, pulling him in closer. Crowley was pleased to see her face scrunch, another orgasm soon to engulf her.

“ _Come for me, darling. I want to feel your cunt tighten around my cock as I empty myself into you._ ” She moaned at the words then licked her fingers and pushed her hand in between them to play with herself. Biting her lip she came loudly, thrashing about underneath him as he slammed into her a few more times before coming himself. He stayed inside of her while he bent down and kissed her deeply, pulling away only when they needed air.

And then all of the sudden they were back to business again. Crowley pulled out his handkerchief wiping his face before handing it over to Meg, who used it to clean herself up slightly. Meg stood up, legs a little wobbly, and pushed her boobs back into her bra and top.  She seductively put her panties back on, making sure to show off her ass one last time before covering it up with her skirt and fixing herself up a bit. Meg wore a smug look on her face while she sat on Crowley’s desk and crossed her legs. “When can I start?”

Crowley looked at her incredulously. She just proved herself to be the _worst_ negotiator ever. Crowley had her in the sack, or let’s be honest here _had his dick in her pussy_ before they could even discuss terms and agreements. She just assumed he would give her the position the moment she slept with him. This girl relies solely on her good looks and underestimates how noncommittal people can be. “When can you start _what_ , darling?”

Surprised, it took her a minute to answer. “The job _of_ _course_. Didn't I prove myself to be a . . . valuable asset?” Crowley just laughed, not really trying to be cruel, but it was funny how a pretty girl will snap her fingers and think men will fall to their knees.

“Well, _Meg_ , I don’t see how you proved yourself valuable – on the contrary – you spread your pretty legs for me before we ever made a deal. Is that how you’ll handle my clients? Are you a whore for _everyone_ , darling, or is it just me?” The look on her face was murderous. For a moment, Crowley thought she might just grab the letter opener off of his desk and try jabbing it in his eye. Before she could open her mouth to protest, he put up a hand to silence her. “Listen, I’m not purely evil. I see that you have potential. Why don’t I make you a secretary instead? I’m sure it’s better suited to your . . . capabilities.”

“That’s an insult. _I slept with you_! And it was good sex – and you’re just going to throw me to the side?”

“I’m just taking a lesson out of your own book, _dear_. I’m a man who _gets what he wants_ but you . . . you didn't even put up a bit of a chase. Giving me everything I wanted within the first five minutes of meeting is – how should I say this – you've gotten yourself fucked both figuratively and _literally_.”

Meg didn't say another word. She snatched her purse off the floor muttering “ _asshole_ ” and marched out of his office, slamming the door as hard as she could when she left. This didn’t seem to faze Crowley. He straightened his tie, smoothed back his hair, and pressed the button on the intercom. “Lilith, _dear,_ that interview didn't end the way I would have hoped. Be sure to let security know not to let Ms. Meg Masters inside or around the building – she might try and blow it up. I’m going home early tonight. _Daddy needs a drink_.” He stood up and walked over to the massive window in his office. The stars were bright tonight – even in the city. It was a beautiful crisp September night – perhaps he should go out for a drink at Lefty’s. Who knows, he might get lucky there too.

**Notes for the Chapter:**

> ;) Much more to come!
> 
> Find me at http://vulcanpride.tumblr.com/ <3


	3. When Two Forces Collide

Dean sighed deeply into his whisky. It was late and he was tired – he really should be home trying to sleep. He was just so angry at Castiel. How could he do this to him?! How could he pick Sam over him?! It was like all the work he had been doing this past year was nothing to him – like their relationship was nothing to him. Dean had been insecure about Castiel’s feelings toward Sam and this was the last nail in the coffin. He tried to convince himself that life would be better without either of them, that he was a lone wolf and didn't need anyone else, but Dean knew lying to yourself never got you anywhere.

He mindlessly watched the TV in the corner of the bar blathering on about philosophy. " _Two opposing forces: Irresistible and unmovable. What will happen if they meet? The unstoppable/irresistible forces stops, the unmovable object moves. They transfer their properties, because as they are infinite neither can be "defeated" but their properties can be diverted._ " Bunch of bullshit to Dean. He didn't like "what if's" but would rather deal in reality - with real people and real things. That college crap was more Sam's cup of tea.

He glanced over at the bar noticing for a third time tonight some older guy looking him over. Dean didn't usually go for the whole papa bear look but the gleam in this guy’s eye caught Dean’s attention. He could tell that this guy was loaded – that’s totally an Armani suit and Dean’s sure he saw a Rolex watch sparkle from under this guy’s sleeve. Maybe he would get lucky tonight and piss Castiel off – show the bastard (and himself) that he didn't need Castiel. He casually walks over and takes a seat next to the man who’s been eyeing him. Slamming the rest of his drink down, he smiles and leans in close and whispers, “ _If you take a picture it’ll last longer_.” No malice or anger – just flirtatious with a wink.

Crowley looks incredulous at Dean for a moment before ordering two more drinks for the two of them. “I would, darling, but I seem to have left my camera at home. Perhaps you can come back to my place and we can have ourselves a little _photo shoot_?” He flashes a smile at Dean, a hungry look in his eyes. It doesn't seem to faze Dean as he casually takes out his phone like he’s already bored with this conversation.

“That maybe an expensive suit you’re wearing but I guarantee you don’t have enough money to pay me for that.” He laughs softly at the surprised look on Crowley’s face – not many people must talk to him that way.

“Are you in sales?” The demon suddenly asked. Dean visibly perked up, giving Crowley a dazzling white smile, his green eyes becoming sharp and _focused_.

“Who’s asking?”

“Crowley, the King of Hell Inc. _And you, honey_?” A flash of surprise runs across Dean’s face but it’s gone so quickly Crowley hardly noticed it. _Oh shit! This is our – was my competition!_ This could be a very good opportunity for Dean. He has to play his cards right.

“Winchester, Dean Winchester. Nice to meet you, _Mr. Crowley_.” Dean reaches out a hand and Crowley takes it. They both shake. Crowley looks at Dean with a bit of understanding in his eyes – _he knows who I am_. Of course he does. Castiel made sure everyone knew that Dean was off limits.

“So, _Mr. Winchester_ ,” Crowley says almost mockingly, “What brings you to this _fine_ establishment? Where’s that angelic boy toy of yours?” Dean barely bats an eye at him. He’s good at keeping his emotions in check, despite what Castiel said.

“Oh you mean Castiel? He wasn't a very _good_ toy so I tossed him away. I need something with a little more . . . _taste_. Quit my job today too. As I’m sure you already guessed.” He raised his drink like a small toast and took another long sip. “Guess that means I’m _available_.” Crowley took that as an invitation and gently set his hand on Dean’s back, softly rubbing.

“What a coincidence! A spot has opened up in my company. I need a top sales representative to keep the other bastards in line. Someone to work _very personally_ with me on high pressure deals. Would you be interested, _Mr. Winchester_?”

“Very,” Dean replied with a flirtatious smirk.

“I’m not asking for too much. Your complete loyalty to the company – _to me_. I've heard about you, Winchester. I know you've done some good work. Why don’t we take things back to my place and we can . . . _discuss_ your future at Hell Inc? If you could . . . _convince me_ of your assets to the company maybe I’ll consider hiring you. I promise I don’t bite _hard_ , love.” Crowley’s hand had traveled lower and lower during his little speech and rested on Dean’s ass. It made the younger man feel _cheap_ , even if he was strangely attracted to the demon.

Dean looked at Crowley with a raised eyebrow, seemingly annoyed by his suggestion, before drinking the rest of his whisky. He pulled out a few bills to pay for his other drinks and threw it down on the table before standing up abruptly. “I can tell you’re not serious and I don’t have time to waste on people who aren't serious,” he pulls out a business card and sets it on the table before sliding it over to Crowley – his fingers gently grazing the demons. He leans in close to whisper in the demon’s ear, “Why don’t you give me a call when you’re ready to talk business, _Mr. Crowley_.” With barely a glance back at the demon, Dean picks up his suit jacket and struts out of the bar into the cold dark night, making sure to stand up straight and tall, showing off his back muscles and curvy ass.

Crowley doesn't know what to do for a moment. He just sits at the bar a bit stunned. He thought for sure Dean would take the bait. The bastard just broke up with his long term boyfriend, just lost his high paying job, was just offered a lay and a job and he backs out because he thinks _Crowley_ was wasting _his_ time?! . . . _That boy knows how to haggle_. Effective too, because all Crowley can think about is how pretty Dean’s lips looked when he wrapped his lips around his glass, how his eyes followed Dean’s throat as he swallowed the amber liquid. Crowley wants it to be around his cock – maybe he should call Mr. Winchester in the morning. No no – too desperate – he’ll wait a couple of days. It’s the first time in a long time that the thrill of the chase sends a little flutter down to the pit of his stomach. He looks fondly at Dean's card before becoming insanely jealous at the craftsmanship of the card itself.  _Eggshell with Romalian type. Look at that subtle off-white coloring. The tasteful thickness of it. Oh, my God. It even has a watermark._ He washes down his drink, leaves a generous tip, and then leaves the bar to go home for the evening with a skip to his step.

**Notes for the Chapter:**

> Comments and kudos are always very much loved and appreciated!!! <3 <3 <3 (Yes, I did in fact quote American Psycho just for kicks and giggles)
> 
> Also if you're wondering: Dean is the unstoppable force while Crowley is the one that cannot be moved (Get it? Get it?!) Okay I'm done now I promise.


	4. With Everything You Say I'm On My Knees, Baby I'm On My Knees

Dean’s more than a little disappointed in himself. He’s ran the conversation he had with Crowley over and over in his head until he was sick of it. He should have done things differently – _he should have known who he was from the start!_ He was kicking himself because he went into that conversation not realizing who he was dealing with. He should have played himself up more. He should have maybe squeezed Crowley’s knee before fleeing off into the night. He should have made Crowley feel like he had the control . . . Crowley was too good a businessman to go after him now – he made himself too unavailable.

. . . Or it was perfect and Crowley will be calling within the next day or so. Maybe he will wait a few days to seem like he isn’t interested to make Dean squirm.

Dean sighs as he walks through the hallway to his condo. He’s got a nice condo, third floor of a 10 story building with an amazing view, but it’s always bothered him that Sam could afford the penthouse on the top floor. Sam was way better with money than Dean – always investing and making smart choices. When he gets to his door he sees a note taped to the front, it’s probably from Sam. Opening it as he walks through the door he reads,

“ _Dean, came by to see if you were okay. Heard about the news, sorry it had to be this way. I tried calling but I couldn’t get a hold of you. Come upstairs when you get home if you feel like it. I’ll be up late. Love, Sam_.” Dean scoffs and tosses the note to the floor, not even bothering to throw it away in the garbage can.

He plops himself down on his leather couch and takes off his layers of clothing piece by piece. His answering machine is blinking with several unheard messages, most of them from Sam. Two are from Castiel, one saying how much of an idiot Dean is – how Dean’s making a mistake – how Dean’s reaction just makes Castiel’s decision even more right. The other sounds like a half assed apology and pleading for Dean to call (" _I'm on my knees, baby!")_. Dean erases them all and then proceeds to strip himself naked and take a shower.

The hot water feels good on his back. It’s been a long day and all Dean really wants to do is curl up and cry under the shower head. He doesn’t though; only because of how incredibly seething he is at his boyfriend – now exboyfriend. He shouldn’t be angry with Sam but he is. He can’t bear to look at Sam, much less talk to him and have Sam try and convince him to come back to Heaven’s Little Angels Inc., he’s so fucking done with all of it.

Dean palms his slowly hardening dick. He tries to rid his mind of today, forget all the shit that’s happened, and just feel good for a little while. He takes a little soap into his hand and slowly caresses the head of his cock until he’s fully hard. His mind drifts to Castiel but he shakes his head, trying to rid himself of the image. He runs through several scenarios before landing on an old favorite – Rhonda Hurley, the first girl who ever introduced him into BDSM and made him wear panties while she fucked him with a strap-on – that image never got old. He imagined kissing her roughly and biting at her neckline before she commanded him to bend over to grab at his ass. She used to love eating Dean out, trying to make him moan louder each time they fucked, making sure to whisper dirty things to him – little encouragements “ _Good boy. You’re so fucking beautiful like this”_ before slapping him hard on his ass making Dean cry out. Dean pumped his cock faster, imagining being bent over and played with like a slut, crying out for _more more more_ until she, he, _whoever_ slammed their cock inside his ass, hitting his prostate in the process.

Dean lifted up a leg, unable to contain himself, and shoved two soapy fingers inside his own asshole. It wasn’t the same. He craved someone else to do this for him. The angle was awkward and it was difficult to jerk himself off but he pumped faster and faster, thinking of Rhonda, of that one night stand he had two years ago ( _what was his name, Henry? Dean couldn’t remember_ ) and as much as it hurt, he imagined Castiel kissing him while fucking him slowly, whispering the sweet nothings they used to say to each other when they first started dating. They hadn’t been loving in sex for a long time – the past few months it was just a hard fuck in between meetings – but when they first started dating Castiel would ride Dean’s ass slowly, pulling out his cock and watching his little hole twitch with need, before pushing back in again making Dean moan and arch, whispering how much he loved him.

The image was too much, it was too painful. Dean forced himself to think of other people –Dr. Sexy fucking him in the hospital’s supply closet – of the man he met today, Crowley, taking him over the bar at Lefty’s while everyone around them watching as they fucked like animals. _Ohhh yeah_ , Dean liked that one. His legs began to shake as he felt his orgasm pull from deep within, he beat himself off faster and faster, hearing himself moan when he thought of himself on his back while Crowley fucked him deeply, bending down to shove his tongue down Dean’s throat. He came at that image, ropes of cum splattering the shower walls, he could feel his asshole tighten and pulse through the orgasm. He stroked himself off until it was too sensitive to touch and then sat down under the running water letting himself rest.

“That was unexpected” he muttered feeling a blush across his cheeks. Maybe he would try and call Crowley tomorrow, see if he was still interested in a fuck. He finished washing, feeling only slightly better but feeling like he could eat an entire tub of ice cream. Oh god and pie. He was so in the mood for pie.

Dean walked around his apartment naked, toweling off his hair as he walked toward his kitchen to get sweets. He noticed the answering machine blinking again and he was not excited to check it, letting himself enjoy his pie and ice cream before listening to what he assumed was Sam once again calling and checking up on him. Or maybe Castiel bitching again.

He poured himself some whisky from his mini bar in the living room and clicked the answering machine. He sputtered out his drink when he heard the sultry voice on the line.

“ _Hello, darling. I know you just left – I know it’s probably not a smart idea to call you so soon after you blowing me off – but I just can’t stop thinking about your beautiful green eyes—“_

Dean felt himself get giddy like a teenager. He couldn’t believe Crowley called him so quickly. He must have made a good impression.

“ _I want to take you out to dinner tomorrow night, 7 o’clock. How does Masa’s sound?”_

Dean had _heard_ about Masa’s. It was an incredibly expensive Asian restaurant in midtown that Sam took his ex-fiancée there to break up with her. According to Sam, she was so happy to have eaten there that she didn’t even care that Sam had caught her cheating and sent her packing. Dean all of the sudden became overwhelmingly nervous, his palms sweaty and his brain running through several hundred scenarios for their date. The rest of Crowley’s message was his his personal cell phone number and a suggestive comment about Dean’s physique. He said he already knew where Dean lived and that he would pick him up unless Dean had any further objections – _arrogant bastard_ Dean thought, but he loved it and couldn’t get enough of it. He listened to the message three times before finally laying down on the couch, suddenly exhausted with today’s events and incredibly excited for tomorrow night. He started drifting in and out of sleep wondering what to wear . . . what to wear . . . 

**Notes for the Chapter:**

> Title is from Ellie Gouldin's Only You! Such a good song! (Kind of random but if you're bored go listen to it!)
> 
> I don't have much written past this point so it might take me a while to upload the next chapter. I've been working on this story for a while now and the first few chapters are finally finished. I actually don't know how long this is going to be! Originally I thought 10 chapters but now I'm like "I COULD GO ON FOREVER" and have several different ways to end the story.
> 
> Kudos, likes, and love is so so so appreciated!!


	5. Save it for Tonight

**Summary for the Chapter:**

> Dean and Crowley go on a date. <3

The next day was a crisp sunny September day and everything was beautiful. Dean had a skip to his step that morning. Things happened so fast but just like the beautiful morning Dean was currently enjoying the events of his last 24 hours were perfect. Everything seemed to have fallen straight into Dean’s lap. Dean jogged feeling like he was on cloud nine. He was so excited for tonight; excited that he had impressed the only other serious competition for his old company; excited for the potential rough fling; and mostly excited to make Castiel jealous. He actually had been expecting to spend the next week depressed about Castiel and searching for a new job that couldn't even compare to his old one. Dean was paid good money at Heaven’s Little Angels Inc. and knew it; it would have been excruciating looking for a job even in the same ball park. But hours after losing his job he gained the opportunity to win over the second most powerful man in New York.

Not in his wildest dreams did Dean expect to meet Crowley in that bar last night. _What was he even doing there anyway?_ That bar didn't seem the place for someone could afford much much more and with a much better clientele. Lefty’s was a place most sales executives went for a drink -- young desperate people trying to make connections. If Crowley was there he was either looking for a night of mingling with the little people or he was looking for tail . . . Not that Dean minded. He really didn't care why Crowley was there but more so that he met him, flirted, and had a date with the rich bastard. He couldn't wait to walk into Masas with him, intending to turn heads.  

Dean wasn't sure what it was about Crowley that attracted him so. He had a sense of authority, ruggedness, and a certain badass reputation that made Dean weak in the knees. He couldn't clear his mind from the image of being bent over and fucked by Crowley, his low raspy voice murmuring commands into Dean’s ear, Crowley playing with him tied up for hours . . .

At least -- from the stories Dean had heard -- he knew Crowley liked tying up his play toys; liked being the one in control. Dean would make sure to let Crowley feel that way tonight. Dean knew how to play just about anyone; with a flash of his pretty green eyes and pearly white teeth, he knew he would have Crowley on his knees tonight. Or if everything goes to plan, Dean would be the one on his knees.

He took a different route than usual in hopes of avoiding Castiel. That was one constant in their relationship: a morning jog around the city. On weekends they used to get breakfast at the cafe across the street from Sam and Dean’s apartment building. The last time they ate together was at the cafe, Dean realizes, and the thought drains the optimistic energy he had just moments before. He remembers the sun slowly rising and the beauty of the moment cast a glow on the memory of Castiel. It had been so early in the morning and the two had very little sleep the night before. Both of them had been goofy and giggly with love and all Dean could remember was how _handsome_ Castiel looked with the glow of the sun at his back in his tight fitting track suit, his eyes looking impossibly blue. The thought of their last happy meal together gave Dean’s heart a sharp pang of regret and longing but with a few deep breaths and running faster to his classic rock playlist, he tried to forget about those blue eyes at sunrise.

Dean stopped at the street corner to catch his breath when he saw them -- his brother and Castiel -- jogging side by side down down Dean's regular route, much too close for Dean’s liking. Dean didn't call out to them like he wanted to. He wanted to scream at them _what are you fucking doing together_ but he knew that would be a mistake and he would look crazy. All of his feelings of jealousy and rage came surging back to him. He always felt jealous of their relationship. Dean was possessive with Castiel, he’ll admit that anyday, but it was difficult not to be when he saw the two of them together, especially lately. In the past month the pair seemed to be sharing secrets and it annoyed Dean to no end. When Sam and Castiel went to Vegas it was very last minute, very sudden, very “important” as Castiel had put it but Dean still wasn't sure exactly who they met or what really went down. Dean couldn't get a hold of Castiel for most of his trip and when he did speak to him Castiel seemed like the last thing he wanted to do was talk to his boyfriend. Like it was so _fucking_ hard to just say ' _hi, I love you, I can’t wait until I’m with you again'_ unless you don’t feel that way. Castiel barely spoke to Dean the week after his return and Sam was so busy with so many new jobs -- big jobs, ones that Castiel normally did himself -- that Dean couldn't even get an appointment with him through his secretary. Did they fuck? Is that why all this happened? Why Sam was getting preferred treatment?

All he saw was red-- his whole world felt focused on this one moment and Dean couldn't look away from where they had stopped and stretched their tired legs. The two biggest, most important people in Dean’s life had betrayed him and they just flaunt it on the street. Right near the place he lived. _Fuckers_. Without further hesitation he slipped back into a crowd of runners so the pair didn't see him returning to his condo across the street.

 

Sam and Castiel stopped outside of the Winchesters’ condominium building, stretching and taking deep breaths. "Doesn't look like he's on route this morning . . ." Castiel said sadly to a very distracted Sam who was more interested in winking and smiling at a neighbor woman of his. Castiel knew this woman, she was one of his top client’s wives and he wondered quietly what Sam was playing at. That client was not one to piss off and sleeping with his pretty blonde wife would certainly do just that. Sam wrapped an unwelcome arm around Castiel and laughed heartily.

"Well no shit -- he's probably avoiding you, Cas. He hasn't been to see me either." They walked at a steady pace, Castiel having trouble keeping up with Sams overly long strides despite the fact that he was tall himself.

"You're not worried?" He asked surprised. It wasn't like Sam not to chase after his brother, even if Dean was having a hissy fit.

Sam shrugged, choosing not answering right away. He seemed cold today, calculated. Like he was on a hunt.

"Am I worried about my grown ass man of a brother? No not really. If Dean wants to act like a child and avoid us then so be it. I know he will come around eventually, he always does, and I refuse to play his games. I have more important things to think of, right partner?"

He left the door to his condo open for Castiel to follow. When he started stripping, showing his muscular physique and tanned skin, his long hair falling into his face, Castiel couldn't help but blush and look away.

And when Sam saw this, he laughed apparently very amused. "What? It's not like you haven't seen it before, Castiel. I seem to remember a very fun night on our trip to Vegas."

Castiel was shocked to hear Sam bring it up. Castiel chalked it up to a horrible drunken mistake, one that he couldn't look Dean in the eye for what felt like eternity. Sam and Castiel both agreed that --

"What happens in Vegas stays in Vegas, I know Cas." He smacked Cas on the ass before walking into his bedroom, leaving his door open as he stripped further. “I won’t tell if you don’t, angel. So long as we keep our agreement.” They stared at each other for a moment in silence, sizing each other up. Castiel nodded curtly before leaving the condo, making sure to close the door with more force than probably necessary.

Sam was acting very strangely indeed. He wished he could talk to Dean . . .

 

That night came sooner than Dean was ready for. He spent the time after his jog maintaining his appearance. Shaving, clipping his nails, making sure he got rid of his secret unibrow, and lathering himself up in a lotion that also made his skin glow like he was born from some greek god. He had done a little bit of homework on dating Crowley by calling up a fling he had a while back with someone who had been used and abused by the demon.

He took what he could from his source, making note of what to do and what not to do on the date, loving the fact that he knew Crowley’s favorite cologne for his pets.

“You sure?” Dean asked hesitantly, wanting to feel out if the man on the phone wanted to sabotage him or genuinely wanted to help.

“Yes. I’m sure. He mentioned it when he insulted the cologne I was wearing --”

“Okay well thanks for all your help, I really appreciate it.”

“You say you’re going to ruin the bastard?”

“Uhh, not exactly but yeah sure let’s go with it.”

“Listen, Dean, I know we haven't seen each other in a while but maybe when I get back from Florida --” but Dean had no intention of meeting the fling again. At best he would have described the sex as unimaginative.

“Hey sorry, I gotta go man, I have to finish getting ready, thanks for all the help!” he said before hanging up abruptly. He got what he needed from the poor bastard and he was positive he wouldn’t have to call or talk to him again.

And with a overly large grin on his face, he continued prepping for his date. Slithering into his old favorite suit (which Castiel bought for him but Dean quickly threw the thought to the side, not wanting to dwell on Castiel any further tonight) he felt better than he had in weeks. This was just like any other deal; he wanted something and Crowley wanted something. Now they just had to play one another until they reach an agreement; an agreement that hopefully would stand in Dean’s favor.

Crowley was right on time, sending a text to Dean letting him know him and his driver were parked on the street outside. Crowley waited outside the car looking up, examining the building before him. When he saw Dean coming down the stairs he smiled and held out his hand for Dean to take. Dean could smell alcohol on his breath, though his demeanor and appearance showed not one sign of drinking. He wore all black, like he almost always did, except for a red carnation on his jacket lapel.

“You look dashing, Winchester. You really do . . . but you're _missing_ something . . . “ He ran his hands over Dean’s chest and shoulders, apparently looking him over to inspect what was missing, but Dean noticed Crowley licking his lips and uselessly fidget with his tie and collar just to touch the skin there. Dean knew he just wanted to frisk him, wanted to inspect the goods. Out of no where Crowley seemed to pull another carnation out of his hand and placed it in Dean’s lapel. “There, we match now. Wouldn't want anyone to think you didn’t have a date, honey. Don’t want anyone to try and take you away.”

With a flash of a slightly lecherous smile Crowley slipped into the car offering Dean a hand to help get in. They both drove in silence to the restaurant, the air buzzing around them with excitement for they had already started to play a game.

 

When they arrived at the restaurant the handsome driver, a young but very tall southerner named Benny, got out and opened the door for the two of them. Crowley muttered what time they should be done and handing Benny a fifty, told him to go get food himself. Dean was sure that was for his benefit because Benny looked as surprised as Dean did.

The two walked unceremoniously into the restaurant and Dean was a little disappointed that there was nothing out of the ordinary. It looked nice but not so nice that only a very select group of people in New York could get in. They walked up to the hostess who seemed to know immediately who Crowley was and after a warm greeting, asked Crowley to wait momentarily while a table was made ready for him. Crowley said hello to several people he apparently knew in the waiting area, at ease with himself and perhaps overly confident to have a pretty young man like Dean at his side. He whispered small helpful notes into Dean’s ear as they waited in the lobby.

"Oh and that's Richardson and his brother; last year he came to me for help with a family way . . .  Got a good deal out of him -- I can use his beach house on Kauai any time I want now . . .” He winked at Dean who couldn't help but smile back. Crowley, pointing to a very prim woman being led to a table, whispered once more, “Oh and that’s Marceline Travis -- helped her with a nasty divorce case a few years back. She’s worth millions and her ex husband was trying to swindle her out of her money. A little help from me and now it's taken care of . . . poor bastard.” He stood there grinning like a mad man, apparently not realizing the disapproving look on Dean's pretty face.

“Did you--”

“Kill him? Oh no, Winchester, of course not. I run a _reputable_ business. We found pictures of him with another woman, that’s all. He didn't get any money and I now have a _very powerful_ friend in the medical industry. He committed suicide you know -- I’m surprised you haven't heard about this -- it was in all the papers . . . " but the grin Crowley flashed during his little speech did nothing to convince Dean of his innocence in Marceline’s husband’s apparent suicide.

Despite the gruesome thought of Crowley ordering a staged suicide, Dean found it endearing that Crowley had to pull him down with one hand on his shoulder and stand on the tips of his toes to whisper to him. Crowley had a powerful charisma that seemed to suck you in, and his little touches and low raspy voice in his ear felt like teases of what was to come later that night. It made Dean feel like he was hot to the touch. Dean liked listening to the demon; he seemed to be a pool of social knowledge and if things worked out tonight then Crowley’s endless connections could be incredibly useful for Dean’s countless career ambitions and life goals.

And then a very broad shouldered large woman came out from the employees door flailing her arms excitedly in the air, walking quickly over to Crowley. She hugged and kissed his cheek affectionately and to Dean’s surprise Crowley returned the warm greeting with a big genuine smile on his face.

"Dean this is Martha, she owns and is the cook in this fine establishment and there's not a prettier woman in New York," Crowley flashed his smile, the words pouring out like honey.

Martha smiled and fanned herself blushing. "Ohhh you sly thing you. You know I'm happily married and even your handsome face can't change that!" They laughed together for a few moments, exchanging stories about Martha’s family (who Crowley apparently knew and was interested in hearing about) before the two of them excused themselves to go see a mutual friend already seated at one of the tables.

Crowley, sensing that Dean was not happy with the sudden abandonment, winked at him before yelling over his shoulder, "Don't look at me upset like that, love, I’ll be right back, just popping by a table for a quick hello. Don't wander off now.”

And that's how Dean was left alone, in an unfamiliar place with no one he recognized, holding Crowley's seat while they waited for a table. He felt unwanted glances coming from several people in the room; some more blatant than others. He made sure to stay away from the very old man on the opposite side of the bench who was eyeing him suggestively even though he had what looked like Barbie hanging off his arm. He made Dean’s skin crawl.

Then the door to the restaurant opened and Castiel walked in and in that moment everything seemed to freeze. He and Dean stared at each other for a few moments, too late to pretend they didn't see each other. Castiel checked in at the desk before walking over awkwardly to Dean.

"So . . ." He began with either no intent or no idea how to finish the thought. When a few moments of silence passed and it was obvious Castiel had nothing to say, Dean sighed annoyed.

"What are you doing here?"

"Running into you, apparently," Castiel sighed too, eyeing Dean up and down, no doubt admiring how handsome Dean looked in his suit and well rested face. He was glad that the jog that morning left him clear headed and he was confident that he looked hot tonight. Castiel would be eating his heart out and it was everything Dean wanted.

Only it hurt to see him somber and looking like he wanted to kiss Dean and kill himself at the same time. He stood a respectful distance away stoically, looking at Dean like he wanted to close the distance.

"I like your suit,” Castiel murmured sadly, “I'm glad you could get use out of it . . . I know it's none of my business but seeing as I'm here with your brother I'm puzzled who you could be with?

"You're here with my _brother_?" Dean asked pointedly, his jealousy getting the best of him. Castiel didn't miss a beat; he had his answer prepared.

"It's a business dinner, that's all. I've known Sam a long time, Dean. He and I are friends outside of you and me. I'm not trying to date him . . .  He's very worried about you by the way. Says you won't return his calls."

Surprised because Dean had been trying to call Sam all week but too stubborn to let it show, he just muttered, "Yeah well . . ." before dropping his gaze seemingly examining an imaginary scuff mark on his shoe. When he looked up he was calm, more confident, less aggressive. He couldn't get mad at Castiel for going out to dinner with his business partner -- even if they were dating. Dean suddenly remembered who he was here with and the thought filled him with more confidence than he thought he could have.

"Who are you here with, Dean?" Castiel tried again.

With a sudden wave of charisma he smiled a beautifully smug smile, before answering with a shrug.

"I'm not sure you'd know him."

"If he eats here I'm sure I do."

Just then, as if on cue, Crowley walked back into the room with a lipstick kiss on his cheek and a drink in his hand. He signaled for Dean to come over as he was being led to a table. Dean smiled, "That's him there. I have to go, he doesn't like it when I keep him waiting. Bit of a _rough bastard_." He winked at Castiel and very slowly started walking away, secretly waiting for Castiel to respond. He seemed to be frozen in place, staring at the door Crowley had disappeared behind.

"You're here with Crowley? _Crowley_?! Where did you two meet? Oh Dean the stories I've heard -- and _you know_  about my brother Raphael and him . . . _No Dean_ , come on! He’s -- he’s a brute! Is this a _date_ or a business arrangement?" Crowley's appearance did what Dean had hopes it would do. Castiel was green in the face with jealousy, he looked positively furious.

"Not that it's any of your business, and I certainly don't appreciate the criticism, but we are here for _business_ , Castiel." Dean said pretending to be angry before smiling again, playfully. "Maybe more if he's lucky," another small wink and then with an air of superiority of someone who had won the conversation, he said his goodbye. "Nice seeing you, Castiel. You look well. Tell my brother _I'm fine_ and that I'll talk to him later." Dean shot one last glance at his ex before strutting away to show how good his ass looked in these trousers. Castiel stood there wordlessly, not sure what to do with himself, while Dean hurried toward his future boss and man of the evening.

The waiter led them to a small table near the giant windows at the back of the restaurant. Masas sat nearly 30 floors up on the top floor of a skyscraper in the heart of downtown. If the food wasn't good Dean could still see people paying good money just for the beautiful view.

"Having fun already, darling?" Crowley gave Dean a mischievous grin over the menu before taking a sip of craig. "Was that Mr. Castiel Milton? What did ol' blue eyes say when he saw you with a real winner?"

Dean flashed his pearly white teeth before licking his lips suggestively. "Not much. He was a bit shocked to see us together.” They gave each other a knowing look, Crowley enjoying Castiel’s misery as much as Dean. “He did tell me very clearly that I should stay away from you. He said you were a _brute_." Crowley laughed warmly and then shrugged, giving Dean an innocent look.

"Who? _Little old me_? Hmm . . . Maybe I am, it depends on who you've talked to . . . and how hard you like it in the bedroom."

The two men laughed and talked through two hours of wine, and amazing food. While Crowley was crude and blunt he made up for it with his charm and wit. He seemed to shine when he made Dean laugh and he told Dean several hilarious stories about his exertions in Europe, including the time he was captured by a medusa like creature before seducing her and her eight beautiful sisters. The main point Dean took away from these stories how much Crowley loved to drink, smoke, and _fuck_. Dean couldn't get enough of Crowley's voice, opting for silence when Crowley would take control of the conversation. Sometimes to make a point Crowley would drop down an octave and Dean would blush and loosen his tie -- suddenly too warm and constricted in his suit.

Dean was very pleased to note that Crowleys found him equally as interesting. He asked Dean many questions about his life: about how he raised Sam, about how he still kept in contact with his surrogate mother Ellen and her daughter Jo, they even talked business to small degree. Crowley laughed at Dean's jokes and most importantly asked nothing else about Castiel. Dean was thankful about it too because he kept throwing small glances at Sam and Castiel at their not-as-great seat toward the front of the restaurant. He made eye contact with Castiel several times and each time Castiel would turn away slightly red from being caught staring. The night was an overall success.

Everyone seemed to like him here too, which was odd, given what he had heard about Crowley. The rumors of Crowley being a bastard at work were known far and wide but the whole staff seemed to light up when he was around. Crowley seemed to know everyone by name and made jokes with more charisma than Dean thought possible for someone so rich.

"Everyone loves you here,” he said appreciatively. Crowley nodded knowingly, signing his name for the bill.

"Always treat customer service employees with respect. It's hard work and people are idiots. I started out as a tailor you know--" Dean noticed the very generous cash tip Crowley left and the two of them made their exit.

Happy with their light conversation and perhaps too much to drink, they passed through the tables making sure Castiel and Sam would see them: Crowley's hand on Dean's perfect ass, Dean shouting loud enough for everyone in the restaurant to hear, " _Save it for tonight, baby_ ".

**Notes for the Chapter:**

> Sorry this took so long! 3+ months! :( This fic is totally not abandoned, it just turned out much longer than originally anticipated. I have several chapters written for the later parts of the story, so I've been writing but it's not in order. XD I have a few chapters to post after this one, once I polish them up. Expect another update in the next few days. :)
> 
> Thank you all for being supportive and commenting on the fic! Hope you're all liking the story so far! I know I'm having a blast writing it!
> 
> P.S. There is PORN the next chapter. I repeat. There is PORN the next chapter. That is all. <3
> 
> Find me at http://vulcanpride.tumblr.com/


	6. Scootch On Over Closer, Dear, And I Will Nibble Your Ear

Maybe it was the wine, maybe Crowley slipped something into Dean's food when he wasn't looking, but Dean was hornier than a high schooler and he wasn't sure how it happened. It probably wasn't helping that Crowley had an arm wrapped around him, playing with his tie in the other hand, and was whispering naughty things into Dean's ear like "I'm going to push you down when we get to my place and I'm going to take you right in the hallway and fuck that pretty little ass of yours." He felt hot to the touch, not able to stand it when Crowley put a hand on his knee. It was too much and he refused to fall apart so easily, so he pushed Crowley away blushing furiously. " _Behave_! We haven't even discussed our business arrangement . . . "

But the idea of Crowley pushing Dean down and having his way with him did a lot for Dean -- he was super up for that and the hard on he was currently sporting showed it. He wouldn't even mind if Benny joined in; he was also incredibly handsome and Dean imagined that Benny could pick him up and throw him up against a wall if they fucked. Benny drove in silence, pretending that he couldn't hear the dirty things Crowley was saying to Dean in the back seat.

He took them to Crowley's condominium in the heart of downtown which was one of the nicest buildings Dean had ever seen. It looked older than some of the more modern looking buildings on the same street but nicer, fancier, and it reminded Dean of 'old money'. The first floor was set in an ivory marble and had what looked like actual gold fixtures lining the walls and ceiling. It looked ridiculously gaudy to Dean and he hated it but as they walked over to the elevators down the hall he quickly recognized several powerful political figures talking and laughing with a popular young TV show host and his sexy young girlfriend.  If he came over more often to Crowley's apartment he could meet more powerful figures than he ever thought possible. He was sure he saw Castiel's father dip around the corner but as soon as they reached that same spot he appeared to have vanished.

Crowley owned the top three floors in the building combining them to make one massive apartment that connected through large wooden spiral staircases. Dean felt his phone vibrate through his jacket pocket and silenced it without looking to see who it was, eager to show Crowley his dedication. Crowley was feeling good. He seemed to be floating on air, like Dean, and couldn't help but reaching out and touching Dean every so often.

The demon put a hand to Dean's back and led him through the apartment to his private living room, just down the hall from Crowley's bedroom on the top most floor. Wooden floors, a brick fireplace, and the dark green wallpaper almost made the living room feel like an old British pub. He even had a dart board in the corner of the room with a picture of Donald Trump taped to it. 

“What did Trump do?” Dean laughed knowing full well that he had signed Trump to Castiel's company when Crowley had been working the guy for years. Crowley glanced over at the game like he had forgotten it was there and squinted his eyes at the photo.

“ _He knows_.” With a flick of his wrist the picture burst suddenly into flames until it was ashed. Crowley made no move like had noticed this strange phenomenon and gestured for Dean to sit down while he made them drinks.

Dean looked around soaking his environment up. There wasn't anything out of place in the apartment; Crowley seemed to go for an expensive but minimalistic feel. There were trophies neatly positioned on a large shelf and photographs on the walls of Crowley with big name celebrities.

Crowley poured two drinks behind the large bar that sat on the opposite end of the room near the door to the balcony.

With Crowley momentarily busy, Dean checked his voicemail nervously excited to find that Castiel had called. He listened carefully and to his surprise Castiel was pleading with him, _begging_ him to come back.  It was movie perfect, right down to the stressed out bargain offered by Castiel "I'll offer you an 8% raise and you can have _my office_ if you come back! Don't make a deal with Crowley, _please, Dean_!"

It was tempting. That was a damn good raise and Dean wasn't sure Crowley would match it. If he were honest with himself he wasn't sure he could turn down a pleading Castiel. He looked so sad in the restaurant earlier. As good as it felt to make him jealous it hurt to think about actually hurting the angel and deep down Dean knew he still had feelings for him. He hadn't been happy toward the end of their relationship and that put a damper on any empathy he might feel for the angel, but hearing Castiel like this made him feel guilty for playing this little game in the first place. He was suddenly worried what Castiel would do if he did sleep with Crowley --

But his inner struggle would have to wait as Crowley plopped himself right down next to Dean on the couch handing him a martini. Dean chuckled into his drink – Crowley was so eager, he couldn't keep his hands off Dean. He acted like he was the one with the power but Dean, obviously, was driving the demon crazy with lust. When Crowley put his hand on Dean’s knee Dean said nothing but he did push his hand away when Crowley moved it too far up his leg again.

“Still no? _Darling, you’re killing me_.” Dean laughed but didn’t pull away when Crowley threw an arm around Dean and gently rubbed the back of his neck.

He wiggled his eyebrows suggestively and in a mocking tone asked, “What kind of _man_ do you think I am, Mr. Crowley?” before leaning towards the demon. Crowley inhaled deeply smelling the cologne Dean wore, drinking it up. Either Dean is just happens to be wearing his favorite cologne or Dean’s a little more than prepared for this evening. He’s done his homework, he plays the game well.

“A naughty one, I can see. Your self control is astounding.” The look he gave Dean was genuinely impressed and Dean, inflating with the compliment, dared to tease the demon further.

"I've been well informed that you, sir, are in fact a _brute_. I must have self control when I'm around you or who knows what evil things you'll do to me." And it pleased Crowley because Dean saw his cheeks redden ever so slightly. Crowley licked his lips and in a split second decision, grabbed Dean by the tie and pulled him in so close their noses almost touched. Puckering his lips, inches away from kissing his new pet, he felt Dean push slightly on his chest to stop him. heard Dean say,

“That job you proposed--”

“Is yours of course --”

“If I sleep with you.”

“ _Obviously_ , pet.”

“Yes but what’s in it for me?”

“I took you for an intelligent person, Dean. _A bloody job_!” Dean laughed, flashing his pretty white smile, making Crowley actually feel hot from how attractive he was when he laughed.

“Yes I know but you're really doing yourself a favor by hiring me. We both know you're really benefitting yourself first and foremost. And what do you get? A great sales agent for your company – _the best by the way_ – and you get to sleep with him? Not to mention the fact that you'll be taking me away from your biggest competitor—“ It was Dean’s hand that landed on Crowley’s knee this time, slowly moving up his pant leg as he talked. Crowley couldn't keep his eyes off of it. He still managed to speak but not with the suavity from earlier.

“Now _hold on_ , Winchester, you quit remember? I’m not taking you away from anyone.”

“Yes but Castiel has been calling and calling trying to get me back. He’s worried _sick_ over it; even offering a raise if I come back. So really I have options . . . and I wouldn't mind seeing the two of you fight over me. Or maybe if you sweeten the pot a little I’ll just decide to work _under_ you . . . boss.”

Dean knew which buttons to press. In the process of his speech he had taken off his tie and unbuttoned his shirt a little – seemingly to relax but really to show off just that little bit of skin under his collar. He didn't miss the way Crowley’s eyes darted straight to his neckline. Oh my god is that a freckle? Does he have them everywhere?! Crowley wanted to leave marks there, wanted to put his hands around Dean’s pretty neck. He hasn't worked this hard for a lay in a long time and in all honesty it was exciting and excruciating at the same time.

“Well what do you want, love?”

“I want my own office. I want job security – you won’t just fire me the moment you’re bored with me.” Crowley chucked at that, he totally fired Henry last year for that same reason. When his blowjobs had become unimaginative, Crowley gave him the boot. “I want a 10% raise from my last salary—“

“That’s _ridiculous_! 3% would be much more reasonable given your current position—“

“What have I told you about wasting my time?”

“Fine, 5% if you're going to whine about it!”

Dean looked at him annoyed with a raised eyebrow. “Castiel offered 8%. Would you care to hear the message? He was so needy; I’m sure you’ll enjoy it.”

“Fine, fine I’ll give you a 9% raise but I want at least three separate occasions where you blow me in my office and when we fuck tonight I want to come all over your pretty face.” It was Dean’s turn to blush but he nodded and awkwardly cleared his throat.

“Only if the blowjobs are in private; no hidden cameras or surprise threesomes . . . “ Crowley’s eyebrows shot up but he smiled and nodded nonetheless. Dean would be a good agent, he seemed to guess what his opponent was thinking . . . Should make sure he doesn’t practice occlumency . . .

“Ruins some of my fun but _alright then_ , honey. Do we have a deal?” Dean nodded and took another sip of his drink. Crowley realized that he was nervous for the first time that night. He probably hadn’t used sex before this to get ahead at his career. So then his relationship with Castiel was emotional. Good to know. “Then let’s seal it with a kiss, baby.” Dean leaned into his new boss and kissed him gently, surprised that the first kiss, the one that seals the deal, felt physically hot to the touch. Impatient, Crowley shoved his tongue into Dean’s mouth exploring his new playtoy and liking how Dean moaned into his lips. A hand shot up to deans hair and Crowley pulled gently.

  
“Good boy . . . “ he cooed before going in for another kiss. Without much effort at all, Crowley picked Dean up in his arms and carried him off to the bedroom up the stairs and down the hall. The surprised look on Dean’s face made Crowley chuckle and mutter “you gotta love that super demon strength . . ." And in a lower raspy voice he whispered, "I hope you're ready for this . . .”

He threw Dean down onto the bed and positioned himself in a black leather chair next to a massive bookcase in the corner of the room. The bedroom was huge but modestly decorated. Not cluttered or even necessarily lavish, but a minimalistic sense of expensive taste. He knew the chair Crowley currently sat in probably cost more than a month’s worth of rent at his downtown New York condo. The curtains were drawn shut but Dean knew that the view must be beautiful. Dean’s attention was brought back to Crowley as he cleared his throat loudly.

“I want you to strip for me. _Nice and slow, baby_. And then when you're down to your knickers, I want you to blow me with everything you've got. Let me see what kind of _whore_ I just paid for.” His smile was lecherous but there was no sting to any of his words. He looked excited, Dean thought, and then realized that he was a little excited too. The stories he had heard about Crowley’s libido . . .

With Dean’s tie and jacket already off, he unbuttoned the rest of his shirt and took it off slowly, turning a little bit so Crowley could see his muscled back, his strong arms flexing. He dropped his trousers quickly, removing his socks next and tossing everything to the side. He made to remove his undershirt, just a simple white tank top but when he started pulling it up Crowley made an involuntary groan and motioned for Dean to come closer. He did so, letting Crowley feel his chest up and down through the tanks thin fabric. Dean bent down to kiss him, liking the way his kiss was less controlled, excited for what was to come, and the way his beard scratched Dean's smooth chin.

Crowley tweaked one of Dean's nipples, and Dean moaned in response, not because it necessarily felt good but because he knew he had a part to play. He wanted Crowley to adore him, so he could get more out of this arrangement, maybe even be his favorite pet at the office. It certainly had advantages with Castiel, not that he really had to work for it then.

Crowley pulled Dean's tank over his head and grabbed ahold of his hips, admiring the muscular disposition of Dean's young, supple body. Crowley opened his legs wider and Dean made no hesitation to get down on his knees in front of him. Crowley palmed himself though his trousers and actually moaned softly when Dean nuzzled his face against his dick straining in his pants. He unzipped Crowley's trousers, fumbling slightly at his belt,  and released Crowley's thick cock and balls from imprisonment. Crowley was packing and Dean took a minute to appreciate fully how large he was, stroking him slowly up and down.

He licked a long stripe up Crowley's shaft, making sure to make eye contact with the demon while doing so, before taking Crowley into his mouth as far as he could go. Grunting from the wet heat Crowley let his head fall back to rest on the leather chair, hands gently resting on top of Dean's head. Dean massage Crowley’s balls gently with his left hand, while continuing his slow pace of sucking his cock. He let Crowley feel his whole mouth, making sure to go very slowly when he dragged Crowley's cock against his teeth and roof of his mouth, making his cock sensitive from the textures and ridges.

Dean continued his slow, agonizing pace and Crowley impatiently thought he was trying to torture him. He positioned Dean's face to line up to his groin, and held his jaw in place as he thrusted up into his mouth. Surprised, Dean choked a little at the sudden giant cock pounding into his face but willing himself to stay still and relax he took deep breaths through his nose. When Crowley pulled back he could see tears staining Dean's beautiful face from the force of the thrusting and moaning at the sight he slapped his cock on Dean's face twice before Dean held him down and sucked down as much cock as he could. He was so pretty while he did it with those beautiful green eyes and dazzling smile, those perfect bow lips...

Dean deep throated Crowley for just a few thrusts more before the demon couldn't take it anymore. Crowley pushed Dean back and walked over to the bed to lay down, motioning for Dean to get on top of him.

“ _I want you to ride my face, baby. I want to stretch you open, make you loose for me, honey_.”

Dean couldn't have possibly become redder. He hadn't ever done that before, with a man at least, it was way too intimate an act for the one night stands he usually picked up and Castiel never seemed to be interested in anything other than old fashioned missionary intercourse. 

He obeyed, turning himself around to slowly jerk Crowley off as the demon pulled Dean’s ass closer to his face, experimentally licking making Dean shiver. Holding Dean’s hips so he couldn't move away, he circled his tongue around his tight asshole and gently prodded the tip of his tongue inside. It felt weird from the position because Dean could really feel Crowley's beard scratch against his smooth skin. It was so intimate, so personal – and with Dean trying to keep his guard up in hopes of not falling apart for a demon who has a reputation of "hitting it and quitting it". It wasn't before long, however, that Crowley had pushed through the ring of muscle with as much of his tongue as he could, seemingly longer than most people’s tongues (gotta love those demonic powers) and ever so slightly grazing Dean’s prostate.

Dean cried out when that happened, starting to get into the pleasure, rocking his hips back and forth across Crowley’s face. Crowley chuckled sending vibrations into Dean’s ass before spreading him with his hands and slipping a finger inside with this tongue fucking him faster. Dean groaned, that little bundle of nerves lighting up making him feel like he was on fire. He soon forgot to jerk Crowley off and sat up straighter to let his tongue go deeper. Before he knew it, he was chanting little praises, his cock so hard it was sticking straight up and leaking desperately against his stomach, his hips snapping back and forth so quickly that Crowley had to hold Dean in place. He felt like he wasn't going to last and shrieked, “I’m gonna . . . !” making Crowley hum appreciatively before grabbing Dean’s cock and jerking him off just a couple strokes making him cum and scream on top of him, cum splattering on Crowley's chest and stomach.

Crowley patted the space next to him and Dean obligingly lay down beside him. Turning his back to the demon he lifted one leg up to expose his wet stretched asshole, still panting from the intensity of his orgasm. Crowley positioned himself to spoon Dean lining up his cock and murmuring into Dean’s ear, making him shiver. In a low husky voice he whispered,  “Was that good, baby? You make the most _beautiful_ sounds when you cum. I want to hear you again, sweetheart. Before we're done tonight I'm gonna make you cum over and over again until you _crave my cock_ in your sweet little ass.”

He pushed the tip into him slowly. Dean was panting harshly, his face and chest still a deep red, his eyes glassy and his legs feeling like jelly. Crowley inched his cock inside until he was buried to the hilt, stopping there to let Dean adjust. Dean’s legs shook harshly but Crowley grabbed hold of the one in the air to steady him and turned toward him for a deep kiss. Dean moaned into his lips and moaned louder when Crowley began moving his hips. Crowley rocked back and forth and it took everything Dean had to just keep breathing steadily while the demon sped up his pace, eventually slamming into him so hard that Dean felt the whole bed bounce. It was incredibly intense at first but Crowley found the right angle and Dean couldn't help but rock his hips in time with Crowley's thrusts, lost in pleasure.

His cock had jumped to life and he felt like he was ready to explode again. He reached down to touch himself when Crowley pushed Dean back suddenly and switched positions, standing up on the side of the bed over Dean, making the him lay face down into the bed, unable to touch his throbbing cock, his legs dangling off the side.

Crowley planted his feet on either side of Dean’s, grabbed his hips to keep him in place, and started fucking him relentlessly pounding over and over again, making Dean cry out in surprise, his hands trying to grab hold of the sheets to steady himself. But Crowley was picking him up without so much as breaking a sweat and Dean realized he had no control over the situation anymore. He had never been fucked like this in his life before, never had a cock this big up his ass, or someone who was strong enough or with enough sense of lust to push him up against a surface and fuck him silly. He was completely lost in the feeling. Taking deep breaths and opening his legs wider for Crowley to fuck him deeper, enjoying the roughness of it all more than he thought he would. He felt like Crowley might split him in two but the harder the demon went the louder Dean seemed to cry for _more more more._  Crowley felt Dean's ass involuntarily clench around him and he fucked him hard through his orgasm. Crowley growled bending down and biting Dean's shoulder hard enough to leave a ring of teeth and a quivering Dean underneath him. Crowley pulled out, slapping his cock against Dean's ass, admiring how beautiful he was with his ass in the air for Crowley. He smacked him hard, his heavy hand leaving a large red mark on Dean's smooth ass. Dean made to get up but Crowley pushed him back down on the bed.

" _No honey, we're not done yet baby. One more, one more for me_."

Flipping Dean onto his back, Crowley lifted him by the back of his knees and fucked him so easily Dean could have been a rag doll. He pounded into him over and over again until Dean was screaming Crowley’s name below him, his face a bright red and his eyes closed shut. The younger man looked as if he was about to lose it at any second. Crowley could see his cock leaking, straining for release and when Dean desperately reached to jerk himself off Crowley batted the hand away and repositioned himself to pound deeper into Dean, bringing their bodies closer together. Crowley sucked at Dean's lip, shoving his tongue down his throat and completely taking over Dean's space with sensual bites and kisses. Dean groaned into his lips, pushing his head to the side to breathe while Crowley continuously thrusted harshly inside him.

" _Please . . ._ " It was barely a whisper in the darkness and Crowley moaned at how needy, how absolutely _wrecked_ he sounded.

" _Tell daddy what you want, darling . . .  What do you want, baby_?"

Dean threw his head back, unable to contain the groan from a particularly harsh thrust. He opened his teary eyes and looked up at Crowley, their faces inches away from each other, his bright green eyes seem to shine even in the dimly lit room and his lips were swollen from biting and sucking . . .  " _Make me cum . . . Please make me cum . .  I wanna . . ._ " Dean's legs trembled with anticipation, he was so needy, so lost in the pleasure, Crowley couldn't stop thinking about how beautiful he was like this. He moaned loudly at the sight and couldn't contain the stuttering of his hips, reaching a hand down to stroke his baby off, since he was _such a good boy_ and listened so well.

Dean came at the touch of Crowley's hand, he had barely stroked his cock when it just spilled over, over too quickly, his body too eager to be swept up in a wave of immense pleasure. Dean panted harshly as Crowley moaned and thrusted into him, less forcefully now that Dean had climaxed for a third time tonight. He whispered to Dean " _Look at me . . ._ " Dean did and Crowley overwhelmed with the sight pulled out of Dean and ran over to his side, slapping his cock against Dean's tired face a couple of times before jerking himself off in earnest with one hand and holding Dean's head down with the other. He wasn't long before Crowley lost it, what with standing over the beautiful disaster that was his new pet, who from under him was whispering encouragements like " _C_ _um for me, cum for me daddy . . ._ " and true to his word, he came all over Dean's pretty face, rubbing his swollen sensitive dick against Dean's swollen lips as he came down from his orgasm.

Both men panting, Crowley laid down next to Dean. Seemingly pulling a towel out of no where, he cleaned Dean up with surprisingly amount of tenderness and care, meaning to for a minute cuddle with his new favorite play toy. He didn't want Dean staying the night, he would have him leave soon, he didn't want to get attached and he could see that already happening. Dean was too pretty for his own good, too dazzling, too . . . Too . . .

"Perfect . . ." Dean said to no one in particular. He had a dopey smile on his face, and Crowley could tell he was going to fall asleep soon.

"I know . . . It was good for me too, pet . . ." Crowley brushed his hand over Dean's head, appreciating the happy moan he got in response. He realized after a few more pets, Dean had in fact fallen asleep and snored gently beside him. Crowley turned off the remaining lights with a snap of his fingers and snuggled in closer to Dean. Okay, maybe an hour nap and then he would wake Dean up and tell him to get a cab home. He couldn't stay with Crowley, it wasn't part of the deal and Crowley certainly didn't let his toys stay too long. He didn't like it when either party grew too attached.

Yes an hour of sleep . . . Then he would wake Sleeping beauty up . . .

**Notes for the Chapter:**

> :3 Hope you're all liking the story so far!
> 
> <3 
> 
> Find me at http://vulcanpride.tumblr.com/


	7. Breakfast at Crowley's and Those Gosh Darn Unwanted Feelings

**Summary for the Chapter:**

> Short fluffy chapter of the morning after. <3

Crowley awoke with a start the next morning to an empty bed and a flushed face. It was that damned dream again; it made Crowley uneasy. He generally didn't dream and when he did they were mostly nightmares from long ago; centuries before when magical creatures fought for territory; where demons and angels fought for reign over the Earth; when they were hunted and shunned from humanity into the darkest dwelling called pits in the most remote regions of the world where no man would dare tread. One of the reasons why Crowley loves capitalism, why demons and angels have thrived in America, is because it changed everything for them. Humanity onced feared the magical as they feared the darkness but greed overcame their fears and humanity's desire created a spot for magicals in the 21st century. Once humanity found out angels and demons had something to sell it’s amazing how fast things changed and how quickly people forgot about the massacres and wars. Nobody cared anymore as long as they're able to get the car they want, the career they want, the boobjob they want. _Anything you want for the small price of your soul._ Humans stay happy and demons and angels become respected and powerful in the business world, but most importantly they gained the freedom to walk the Earth no matter if you had horns or a halo.

This dream was different though; there were no monsters, no wars between angels and demons, no bloodshed, no misery -- instead it was a dream of heavenly calm and serenity.

Crowley sat on the beach of a small lake surrounded by trees with a child asleep in his arms while he watched the sun go down. The golden shimmer of sunshine reflected beautifully on the water making the waves sparkle. There was a figure near the water but Crowley could not tell who they were or what they were doing there. The first time Crowley dreamed this horrifically serene dream he brushed it off to a bad night of whores and too much cocaine but since that night three weeks ago he’s had this dream nearly every week since. He tried to forget, tried to ignore it once more. He rubbed his eyes from sleep and looked around for any signs of Dean. He saw nothing but the white undershirt forgotten by his leather chair near the bookcase.

Crowley hadn’t let someone in his real personal life in a long time and he meant to keep it that way. Last night went a little too far; he should have woken up Dean and made him go home. This wasn't the first person he had brought back to his condo, not even this week, but this was the first person in years that he allowed to stay over for the night. He already hated sleeping; in the pit there was no time for relaxing only a steadily moving clock to chaos and destruction. On Earth things seemed to slow down. Taking a human form meant he had to sleep; had to rejuvenate and relax to take care of his meatsuit otherwise he would need a new body every few days. He hated the idea of sleeping; it left him vulnerable. This was the same reason he hated cuddling. Opening yourself up to someone, wearing your heart on your sleeve even for just a few hours, was a chance Crowley was not willing to take. He only let Dean stay the night because he’s pretty when he sleeps. He certainly does not have _feelings_ for the boy. He’s just a fun toy to play with.

Getting up from bed Crowley tossed that idea to the side along with the black silk boxers he was wearing and stretched his old bones. His thoughts drifted to breakfast and coffee. He washed his face and put on a robe before picking up Dean’s undershirt shoving it into his face and inhaling deeply. It reeked of Dean, he reveled in the smell, it made him excited. He put it in his robe pocket so he wouldn’t forget to take it with him to work. _Embarass Dean a little in front of the other guys, put him in his place. Remind him that daddy’s the one in charge._ But when he opened the door to the hallway a strong smell of bacon and coffee filled the room and Crowley heard someone in the kitchen. Dean hadn't left, he was still in the apartment, Crowley still wasn't alone . . .   _Oh god. Awkward._

Marching over to the kitchen determined to scold Dean for using it in the first place, he stopped suddenly at the table, shocked to find that it had been set with cutlery, French toast, fruit, and a pot of coffee waiting to be poured next to two empty cups. He saw through the open kitchen door that Dean was busy frying the last bit of bacon, wearing nothing but his tight fitting boxer briefs from the previous night. He looked delicious, and Crowley thought of something he would rather do that eat the food before him. Crowley cleared his throat loudly, which Dean heard and after fidgeting with the heat on the stove, came out with a plate of bacon.

Crowley gave an insincere smile to Dean's seemingly genuine one, and gestured to all the food in mock surprise. Dean sat down and made himself at home, pouring himself coffee and grabbing himself a portion of French toast.

"What? You don't eat breakfast? You sure had plenty of food for it." He was cheery, ignoring how Crowley hadn't sat down yet and awkwardly hung around the table, like he was too scared to come too close because Dean might give him cooties.

"I just wasn't expecting such an . . . _e_ _xtravagant_ breakfast." It was Dean’s turn to look surprised.

"If I were going for _extravagant_ I would have gone more for eggs Benedict or hand made biscuits and gravy . . . This was easy-peasy, I woke up just a little while before you did, threw something quick together so we weren't late for the office." He smiled at that, like he had won a contest with no one in particular. Crowley tried hard not to find it endearing.

With an overwhelming unfamiliar feeling of warmth, Crowley sat down and started on the breakfast Dean just "threw together", though it was against his better judgement. It was delicious and Crowley was sure Dean was lying about it being easy to do. He was sure the younger man was trying to appease him. "Do you cook often?" He found himself asking though his voice sounded distant, unfamiliar. He was uncomfortable, this was too intimate.

"All the time. I _love_ cooking . . .  I raised my little brother and I guess I had to learn it early on." Something stung from the words, Crowley could tell by the sudden dip in Dean's dazzling good mood. Noticing the silence and that Crowley was looking to him curiously now, Dean flashed another smile and added slyly, “I make a mean cherry pie too.”

"It's delicious, thank you for breakfast. I honestly wasn't expecting you to be here. When I woke up the bed was empty."

Dean let out a little sneer at Crowley, " _Are you sad I didn't stay in for a cuddle, baby?_ "

Crowley laughed but he felt no humor. Something tingled in the pit of his stomach and he knew it had nothing to do with the food. He hadn't been this intimate with a person in a long time. Although he was enjoying it, he was starting to feel anxious that Dean was still there and the room suddenly became much smaller. He needed space, he needed Dean to leave. But Dean was chatting casually about random things, asking questions that he didn't seem to need an answer for, mostly excited about his new office and title and Crowley realized he couldn't bring himself to kick Dean out. Just as he had been so pretty sleeping next to him in his giant bed, he found him too pretty sitting and eating and smiling to say anything.

But Crowley had to leave after only another ten minutes of talk, he had to get some space, so after tastelessly finishing his plate he excused himself for a shower and left a slightly dejected Dean alone in the dining room. He spent longer than usual under the hot water, relieved to find that Dean had vacated the apartment when he got out of the shower. A quick note had been written and left on the table, "Going home to change, I'll see you at work xoxoxo -- D"

Crowley stated at the little piece of paper, at those little x's and o's and an unfamiliar warmth spread to his head. He felt better than he had in years but at the same time felt like he could vomit.

**Notes for the Chapter:**

> Just a small fluffy chapter to set up for later chapters in the story. :) Just an FYI for everyone because I have so much plot written down for later chapters, this story is definitely going to be like 30 chapters so we're not even a fourth of the way over for what I have planned. It's slow, and I'll be writing other things too so thanks to everyone for sticking with me on this journey.
> 
> It's still a work in progress and I'm trying not to update any chapters until they're completely done but when I get more deeply into the plot things might have to change a little here and there. Again, thanks for patience and support. :3
> 
> I love it when you guys comment and kudos! Not going to lie it makes me feel great! Thanks to everyone who is doing so, I love reading what people say. <3 <3 <3
> 
> Find me at http://vulcanpride.tumblr.com/ <3


	8. Something Extra

**Summary for the Chapter:**

> Dean's first day at the office.

Dean dressed in a sharp blue suit with a simple red tie for his first day at work. He was pleased to note that Crowley didn't live too far from his own apartment, making it easy to head home and change. He was able to run down just a few blocks to his complex and he barely broke a sweat. He was surprised that he didn't feel sore from last night’s fuck fest and the thought of last night left a big stupid grin on his face. After showering, shaving, and changing, he looked himself up and down in his full length mirror making sure his looks could kill, wanting Crowley to drool at the sight of him.

He had been surprised by Crowley this morning but it was a good surprise. Dean found out a lot about him during their little breakfast even though the demon didn't actually say much. He realized Crowley doesn't cook often otherwise he would know that French toast and fruit is easy to make, and that Crowley didn't have many people over to his apartment or he wouldn't have been so uncomfortable with Dean. Dean felt the anger in the air when Crowley walked into the kitchen to yell when he was making breakfast but for whatever reason Crowley at least tried to seem unperturbed. It was very obvious by the demon's demeanor that he was a very private individual. Crowley might not have realized how much his attitude changed that morning and Dean found it funny that the best salesman in New York couldn't handle a young beautiful man eating breakfast naked in the apartment. He certainly didn't seem shy the night before.

Dean didn't know why Crowley seemed uneasy but one thing was for sure: the guy knew how to fuck like a _champ_ and Dean was ready for more. Dean had never been pleasured so fiercely before -- so _passionately_. Even though it started out as Dean trying to play favorites he now felt a strong connection to the demon and wanted more of him -- or at least a few more fucks out of him to help get over Castiel. There something about him; he just seemed to radiate sexual energy and when they were together he felt like they were the only two people in the whole goddamn world. Maybe that was an effect of the booze -- maybe he’s remembering everything more pleasantly than it really happened. Dean's still not sure if Crowley slipped something into his drink because he definitely still feels a little weird but a good weird -- like the world is a little brighter and Crowley is the the sun. Maybe Crowley slipped him some ecstasy for kicks.

So while Dean came to the realization that he actually had developed a real old fashioned crush on the demon, he also realized that Crowley needed space, normalcy, and a return to business in their relationship. He didn't want to come off as needy and scare his new boss off. ' _Self control_  ' he told himself. He made several mental notes for next time, ' _don't bring up your date, play nice (at least the first day) and don't let people use your history with Castiel against you especially Crowley_.'

While walking up to the building everything seemed to sink in. How odd it felt to walk down the same road to Heaven’s Little Angels -- to Castiel -- and how surreal it was to cross the street and march up to Hell Incorporated. Heaven looked more like a large church building with a silver complexion and large angelic statues in the front beckoning travelers to walk inside their big golden doors. Hell Incorporated looked much more like it's surrounding buildings: all dark with tinted windows. The building itself was made to look like a modern dark tower comprised of hundreds of tinted black windows. The building countered the angelic statues across the street with two huge Hellhound statues guarding the obsidian black doors, vaguely resembling the Chinese guardian lions. Dean had never taken the time to notice the details in the statutes before -- that the ball under the male's foot was actually a miniature Earth and what was usually a cub under the female's giant paw was a shriveling human child. The statues made him uneasy -- which he was pretty sure was exactly their purpose. 

Dean had seen the building a million times before but never, not once, had he stepped inside. Taking a deep breath and giving one last quick glance toward his old life, he marched in to meet his new world with confidence.

 

He walked in slowly taking time to memorize his surroundings. He tried checking in at the front desk, about to give the assistant a dashing smile and knock her off her feet, but she took one glance at him and said, "Hello, Mr. Winchester, we have been expecting you. Go down the hall to the elevators on the right hand side to the 54th floor. Mr Crowley is busy until this afternoon with conference calls so go see Lilith, his personal assistant, and she will show you to your office." He closed his mouth which was hanging open, so ready to be suave and charming. He was disappointed; feeling struck down because he couldn't dazzle the girl behind the counter. At Heaven's Little Angels everyone instantly liked him for his charisma and his beautiful white smile but glancing around at the employees hustling and bustling he realized those tricks wouldn't work here. _Everyone_ was pretty, physically fit, and sharply dressed. It was slightly unnerving. He didn't feel like the most handsome man in the room anymore and though he hates to admit it, being attractive actually had serious perks in his last job.

Following the front desk assistants instructions he found himself alone in the elevator with an older man who watched him intently. He looked familiar . . . but Dean couldn't put a name to a face, so he nodded curtly at the man and said nothing. Dean could feel the man staring, his gaze searing through Dean's back. In the reflection of the silver elevator walls he could see this man's eyes glowing, gazing at Dean hungrily. His snow white eyes matched the vibrancy of Dean's own apple green eyes and even when he turned and made eye contact -- to give him a quizzical look as if to ask, ' _do you have a problem?'_   The snowy eyed man stared unforgivingly at Dean like he was trying to reach deep into the young man's soul. Whatever this man was trying to do Dean instinctively didn't like it and he wasn't about to let this dickwad push him around.

"Do I _know_ you?" he asked calmly, trying to remain impassive.

"No but _I know you,_ Dean. I knew your parents -- your father in particular. _Interesting_ man. My name is Alastair -- I'm _sure_ you've heard of me." The name rang in Dean's ears and yes, he definitely knew that name. Alastair was a demon retired from Hell Inc generations ago and so inhumanely powerful and hateful that the whole damn state of New York knew to stay out of his way. Dean had heard countless stories but they were so insane that he chalked them up to years of inaccuracy from years of being retold. Alastair was famous as a general in the war against humanity when magical beings were hunted and slaughtered.

Alastair reached out a hand to shake and Dean reluctantly took it. He felt a small shock -- like a current was running through the snowy eyed man's fingers. "Apologies. In my old age I have trouble keeping my powers contained in my vessel."

"It seems like it's time for a new meatsuit." Dean tried to seem nonchalant, nonplussed.

"Yes, I believe it is." Alastair's unforgiving stare told Dean it wasn't working.

"You knew my dad, huh?" He tried a different tactic. Keep him talking, get him distracted, just make it out of the elevator.

"Yes. Yes I knew both your parents actually. I even saw you and your brother when you were just children. Your father and I worked together under the Miltons before joining Hell. He died shortly after. Such a tragedy, dying so young." There was something in his voice; something venomous and quiet hidden in his condolence that made Dean think of a snake in the grass waiting to strike. It was several seconds of silence while Dean wondered what to say.

"Do you work here? With Mr. Crowley?" He already knew the answer. 

Alastair laughed loudly, genuinely amused with the notion. It sounded dry and dark and it reminded Dean of a serial killer he had seen on TV laughing about the people he had tortured and killed.

"I most certainly _do not_  for Crowley. We have business on occasion." Silence filled the small lift again and Dean cleared his throat to break it. It felt like an eternity but they eventually reached their destination. Dean was dismayed that Alastair stepped out of the elevator with him on the 54th floor but instantly relieved when he appeared to walk down the opposite hallway. He called over his shoulder strutting down the hallway, " _Nice_ to see you again, Mr. Winchester. I'm sure we'll run into each other again _soon_." Chills ran down Dean's back. He didn't like the sound of that one bit and would avoid it at all costs.

 

He could see Crowley's office from the elevator; it was at the very end of the hall and the doors were very unique. All the other doors looked to be made of a deep brown wood -- mahogany or probably some expensive type of wood that's endangered over in a part of the world that America doesn't care about -- but Crowley's were made with what looked like obsidian rock with chunks of gems and crystals imbedded into its design. It was smooth and cool to the touch with large iron handles. In gold writing on the front door it read, "F. Crowley -- Playboy, Billionaire Devil -- Maker of Both Dreams and Nightmares."

Distracted, Dean didn't hear the young thin blonde woman slither behind him and it made him jump. She smiled innocently and introduced herself as Lilith -- Crowley's right hand man -- woman -- demon -- whatever -- and his ex girlfriend. She looked Dean up and down and muttered a small praise under her breath that Dean thought was "Nice pick," before sitting down at her desk, unlocking the middle drawer with a key laced around her pretty little neck, and pulling out an envelope with Dean's name written on it in big bold black letters. Lilith silently commanded Dean to walk with her to his office.

Dean felt a surge of disappointed that he wouldn't see Crowley until later that afternoon, especially when he knew how close he was to him -- just behind those eerie looking doors. He followed Lilith to his office on the 44th floor and finding himself in another awkward situation in an elevator as Lilith looked him up and down like she wanted to eat him alive.

Halfway down the hallway was Dean’s office; the door already had his name printed in gold in a neat typewriter font. Maybe it was just the excitement of the occasion but his door and his door alone seemed to glow and a sudden wave of enthusiasm overcame his sour mood from moments before. Lilith handed him a set of keys and before strutting back down the hallway to the elevators she told Dean, “Call me on the intercom if you have any questions, kiddo.” Dean waited until he couldn't see Lilith down the hallway before taking a deep breath and unlocking his office door.

He stepped inside but was immediately surprised by a man standing by the back wall, which was really just a giant window with a beautiful view of the city and the sunrise. The man had long silver blonde hair -- slicked back looking like an adult Draco Malfoy. He was dressed in the finest clothes -- Dean recognized the brand of his shoes and tie -- and his high cheek bones and lack of much of a chin gave him a hollowed out appearance. He turned around and smiled widely at Dean but he could detect a hint of malice, a bite to his manners, and also he most definitely was a vampire. He gave Dean an unnecessary long once over and Dean noticed there was a package on his desk, neatly wrapped in black wrapping. The card attached was in this man’s hands; he had obviously been reading it.

“Can I _help_ you?” Dean asked professionally, trying to mask his irritation. He pointedly looked at the note in the man’s hands who, realizing he still was clutching it, grinned sheepishly.

"Sorry, mate. Curiosity got the better of me. Just wanted to see who it was from. So you're whom Crowley gave the Rosalin office to?” Setting down the card he strutted over to Dean, who had not moved since he first walked into his office. The door remained open in case Dean had to yell or shout. The last time someone looked at him like the way this man did -- he had an attempted rape case on his hands.

“I'm sorry, _who_ are you?”

“Kent Marshall, I work five stories _under_ you.” Dean didn't miss the small dip into anger hidden in the words.

“Dean Winchester.” They shook hands, both gripping unnecessarily tight. Dean noted how close Kent was to him; how he felt like he was trying to push Dean out.

"So tell me. How does it feel to _whore_ yourself out to one of the most powerful men in New York?"

" _Excuse_ me?"

“Listen, I'm not sure what kind of _games_ you're playing at with the boss but it took me 8 years to climb up the ladder here and you swoop in and take the best _damn_ office! I've been one of the fastest people to get promoted to top executive. The human who worked in this office before you worked at the company for _30 years_ before he retired. Other people wanted this office, people who have worked hard. I wanted this office.”

“Sounds like a problem you need to bring up with Mr. Crowley. In fact why don't you leave and go see him now?" Dean could feel that Kent was seething under his outwardly calm exterior -- something Sam was particularly good at but Dean always noticed. He couldn't resist poking the bear. "Hey, aren't you supposed to be in bed right now, _buddy_? How's the sun feeling for you, _Vamps_?” But Kent apparently didn't hear him because he continued to step into Dean’s personal space and Dean being stubborn as he is (and knowing that guys like this need one or two times of standing up for yourself and they're done) refused to move back.

Dean wasn't sure if Kent was about to kill him or kiss him.

“You better just watch yourself here, son. The rules here at Hell are a little different from whatever _butt-fuck_ town you're from. We have ways of getting what we _deserve_ here.”

With that threat lingering in the air Kent made a sudden movement to scare Dean like they would butt heads but Dean stayed unwavering and just remained silent as Kent strut out of the office.

With a big sigh a sudden itch to call his brother overcame Dean. He sent Sam a quick text (which is how he normally apologized for running off and not talking). _Call me when you can_.

He walked over and sat down at his new luxurious desk trying to forget the asshole who just left his office. It was made of some expensive looking hardwood, painted in a deep brown with forest green and gold accents. Slightly rustic looking for the more modern office but Dean liked it. He was incredibly excited to find out he had supplies ready for him in his desk including a laptop computer and an iPad mini, neatly tucked away in one of the larger locked drawers.

He picked up the opened card that came with the small wrapped black box and was happy but not surprised to find that it was from Crowley. Inside was his undershirt that he had left by mistake and a carefully wrapped little silver framed picture.

 

' _Dean,_

_You left this at my place and I forgot to give it to you this morning. This picture I found while I was going through the company’s old executive photos. Once you're settled in go see Ruby on floor 51 for your first few assignments. She’s going to ‘train’ you until you're comfortable here. Don’t be late for the executive meeting at 2PM in the meeting room down the hall from my office._

_See you then, Pet xoxoxo -- C'_

 

This guy is more flippant than a US senator.This morning he was so cold and now he’s giving me gifts and writing little cute x's and o's on cards. 

Dean cut open the wrapping from the picture and was shocked to find that it was of his parents when they were young -- long before they had Dean or Sam. They was standing outside of the building Dean was currently standing in -- a smile frozen on their faces and several people in the background that Dean did not recognize -- except for one man who was undoubtedly the man who harassed him in the elevator earlier, standing in the corner of the photo with those bright eyes that made Dean feel so uneasy.

He had no idea his dad had worked here. Dean knew he had worked for the Miltons, that's one of the reasons Sam and him had such good standing with the family. He died when Sam was born from a ' _terrible accident_ ' his mother always said, and she died only five years after that. They knew very little of their parents. He felt teary eyed and took a long deep breath to calm down. That was a very nice gift from Crowley and perhaps more intimate than the demon meant it to be. Dean wondered if he knew how much it really meant to him or if he had just by chance found the photo and gave it to Dean without a second thought.

Before leaving his office he fiddled with his new personal coffee/espresso maker, discovering shortly after that he had his own hidden bathroom (you had to high five the picture of a hellhound -- which Dean did just out of sheer silliness and was utterly shocked to find that it opened the wall revealing a large porcelain bathroom included with a tub and his own vanity). He chose to take the stairs to meet Ruby, who turned out was much nicer than some of the other people here and it made Dean feel better -- though it made him trust Ruby less. He could handle it if everyone openly hated him but if a few people were nice, and Dean likes nice, then they might try and manipulate him later on. He was kind to Ruby, and she was kind to him, but he felt like he couldn't trust her.

“Anything interesting happen to you yet?” She gave Dean a knowing look over her reading glasses.

“A lot of people want to know who I am and what I'm doing here or they already know me which has been a _trip_." Dean thought for a moment about the man in the elevator -- about his glowing white eyes. Then thinking of another man who he passed on his way down to meet Ruby, he laughed and said, "And some guy told me my _ass was grass_ and he wants to _mow_ it.” Ruby laughed covering her face with her hand before she composed herself, muttering "Oh, Steve . . ." (apparently already knowing who said it) then she continued showing Dean around the building and explaining what his expectations were. She showed him the break room, the cafeteria, the hall of fame, and she told him gossip about some of his new coworkers.

"Is sexual harassment a thing here?" Dean asked after hearing several unsavory stories about office relationships. Ruby smiled sweetly, moving her long brown hair behind her ear.

"We're considered a religion so we are specially exempt from the government in a lot of matters. While we can't like -- you know -- physically attack anyone or anything -- but if people say rude things or try and make you do weird stuff -- honestly it's covered in a lot of their contracts. Some people have actually _requested_ to be able to harass certain individuals when they first started working here."

"And Crowley will just let that happen?"

"It’s _Mr. Crowley_ , he hates it when his underlings become too cozy with him and he doesn't care about a little fun --  _if you have something to offer him._  Something that he wants more than keeping the peace." Dean appreciated her honesty and they continued walking and chatting, Ruby putting her arm around Dean's like something a kid sister would do, it felt perfectly harmless.

 

The time seemed to fly by and 2PM came sooner than Dean thought possible. He had been busy learning about the building, about its history, policies and rules, and most importantly about the most lucrative clientele list that had yet been claimed. There was a room filled with books of names of people who would be of great value to the company but had yet to hand over their souls. Some of the names were sharpied out with dates of when they signed up -- others were highlighted in orange as "priority" targets. Dean was shocked to see how well organized the room was -- books by location, then sorted alphabetically with detailed information about each potential client. He was nervous walking into his first executive board meeting and so thankful that Ruby had followed him to the door before waving goodbye and returning to her floor.

Dean noticed Kent as soon as he walked in the door but didn't give into his little staring game. Instead he shook hands with several  men and women introducing themselves to him, all apparently eager to make friends with the new comer. Dean saw at least two vampires and what he was sure was a werewolf from his clawed hands and golden eyes. Crowley entered several seconds later nose deep in a packet of papers ignoring the hellos thrown his way and sat down at the head of the table. Everyone took their seats and Dean noticed in meeting and greeting everyone he didn't save a good seat and sat on the opposite end of where Crowley was.

“Alright monsters, let’s get started.” Crowley announced finally looking up at the eager faces of his employees. “I think Lucas has a presentation about profits for this last quarter and then we have to go over some new rules from HR about sexual harassment. We can no longer make Brent eat bananas to entertain us. It’s _officially_ written in his contract now and I have a shiny new watch.” Crowley stretched out his arm to show everyone sitting at the table. Dean noticed a man sitting on the opposite side of the table that looked very dismayed. He hoped that was Brent missing his watch and not whoever made him eat bananas. Dean wished furiously that he could make a few amendments to his own contract now.

Crowley seemed to sense the dismay Dean felt; he glanced over to Dean for the first time making eye contact and winking. He stood up and walked over behind him, pulling his wheely chair out from the table and pushing it toward his own seat. He spoke while they awkwardly made their way to the head of the table, every single one of them glaring as they passed, "And last but not least, ladies and gents, this is our newest associate Mr. Dean Winchester. This is _John Winchester’s_ boy so treat him with respect. He’s in a transition period -- just left Heaven’s little Angels -- so I’m sure we can learn a lot from Mr. Winchester. I'm sure you are all _e_ _ager_ to show him the ropes, but his training will be under _my personal_ supervision." It wasn't blunt per se but Crowley couldn't have been clearer than if he had said ' _Hands off, he's mine'_.

He stopped at the end of the table and just pushed the row of chairs down, everyone knocking in together so Dean could sit next to him. Crowley hovered over Dean for a moment, his hands landing on his shoulders with a gentle squeeze, and Dean couldn't do anything but smile an empty smile at the table of lecherous men and women, black eyes looking like they wanted to devour him. Their seemingly kind introductions and salutations were lost as monstrous jealousy took over and Dean wondered if he could be left alone with any single one of them. He was honestly not hoping for special treatment like this . . . it wasn't going to go over well for him and he was really hoping to make friends -- at least connections -- to get settled in.

And then the next two hours were agonizing. He sat through the insanely long presentation, furiously writing notes, frustrated that each slide had so much useless text. Whatever doofus that put together the powerpoint was too focused on big flashy animations and sounds; it was so obnoxious that Crowley muted the computer and made him skip a lot of it. Dean tried to keep up with his notes on his little pad of paper, frustrated that he didn't bring his iPad. Dean could barely keep up with writing his notes.

“ _Dean_ ,” Crowley said suddenly, making him jolt. “Do you have _anything_ you want to add today?” Crowley looked curiously to Dean, like he was trying to challenge him. _Go on impress them_ . . .

“Yes, thank you Mr. Crowley.” Dean awkwardly cleared his voice and stood up to the front of the room behind the podium. All  eyes were on him, he tried his best to look confident, to fight the nervous butterflies fluttering around in his stomach. “I’m thankful for this opportunity to help the company grow. I learned a great deal from the Miltons. I learned what to do and what not to do in expanding and maintaining a loyal clientele list. I believe the Miltons were too focused on finding big name clients. And don't get me wrong -- we need them because they have the money and resources and _power_ and we can obviously use that to our advantage. But what I think both companies, Heaven and Hell alike are lacking, are _connecting_ with the everyday people and making ourselves more readily available to the masses. Yeah we might have a celebrity’s soul but can we get the soul of _everyone_ in a poor working class family? A mom, her three sisters, her kids when they grow up -- _our market builds itself_. Generations and generations of clients. Everybody needs something. So let’s make ourselves more readily available to fulfill those needs and rake in the numbers. That may mean setting up shops across the US -- maybe around the world -- but we can even market that as job creating -- it actually _would_ be creating jobs -- for the great people of America.” He gave a corny smile and a wink to a female demon close to him who blushed and everyone clapped enthusiastically.

Crowley sat back impressed that Dean was so bold so quickly, not just a kissass like so many of his predecessors. He spoke his mind, he threw down what he had and wanted to work through it.

“Very nice, Mr. Winchester. I'm glad you've already been thinking about this. I wasn't expecting such a show.” He genuinely seemed pleased, and Dean was happy to note that Kent looked murderous.

“You ask me to do something and I'll get it done.” He flashed his brilliant white smile and he knew in that moment that half that room was swooning for him and the other half were plotting his murder.

 

Everyone shuffled out of the office after the meeting ended but Crowley grabbed Dean’s arm and asked him to stay behind. Dean made eye contact with several coworkers, obviously transfixed on how quickly Dean had gained favor from their boss, jealous that he was asked to stay and chat with Crowley on his first day.

But Dean had a feeling what this was _really_ about. He could see the hungry look in Crowley’s eye. Dean looked so handsome in his suit -- so cocky and confident. Crowley wanted to make sure Dean knew his _place_.

“I believe -- _and stop me if I'm wrong,_ ” Crowley began in a low voice, “that according to our _contract_ you owe me a few blow jobs.” He motioned for Dean to kneel in front of him but Dean stayed put.

“I believe -- _and correct me if I'm wrong_ ,” Dean teased, taking off his suit jacket, loosening his tie, “I believe the _arrangements_ were to be in the privacy of your office. I didn't tell you I would just slut it up just _anywhere_.” The tone in Dean’s voice made Crowley think he would do just that.

“You’re hashing out technicalities with me, darling?”

“What do you expect? You hired the best. We had a _contract_.”

Crowley pulled out a long piece of parchment paper seemingly from nowhere and Dean knew instantly it was their contract: a magical copy of their conversation the previous night. He was searching for what was said and the surprise on his face made Dean feel giddy.

“You’re right . . . I specified in my office . . .” He looked up at Dean impressed and slightly disappointed. “Let’s move things to my office then.” He made to get up but Dean pushed him back down and sat in his lap before throwing an arm around him.

“Maybe this can be something . . . _extra,_ ” Dean played with Crowley’s tie while he talked to him. He could feel Crowley’s cock straining against his pants for release -- so horny so quickly.

“Extra?” Crowley kissed Dean from his cheek down to his neck, unbuttoning his shirt as he went, biting at Dean’s shoulder when he fully freed him from his shirt. His hands were everywhere and Dean moaned and writhed in his arms.

“Ex -- Extra,” he choked out while Crowley kissed down his chest and bit at his nipple. Crowley suddenly stopped and looked into Dean’s eyes, half teasing and half accusatory.

“How do you expect me to pay for it, pet?” Dean bit his lip trying to come off as cute and Crowley looked like he just wanted to throw him down and have his way with him.

“You'll have to let me think about it,” Dean answered coyly. Crowley tsked at him displeased.

“ _Come on_ , honey,”

“Don't worry so much about it. When I have something I want from you then I'll ask it. For now, you can start by shoving your cock down my throat and then _fucking_ me on this table. We'll see how things go from there.”

Crowley didn't miss a beat. He shoved Dean down to his knees and spread his own legs wide before freeing his thick cock from his pants. Dean took a moment to regard Crowley's thick length before shoving as much of it into his mouth as he could -- trying to relax and deep throat him to get him wet. He went slowly, grazing his teeth along the head and shaft. Crowley watched every minute of it -- his eyes were transfixed like he was worried he would miss part of the show. Dean knew how sexy he was on his knees, how his bow lips looked wrapped around Crowley’s dick. Dean made sure to make an obscene noise when he pulled off, slapping it against his face and loving the moan that escaped Crowley’s lips.

Crowley couldn’t take much of it for very long. He picked Dean up and threw him down on the table suddenly, laughing softly when Dean protested at the surprise. It just made Crowley want to fuck him even harder. They made quick work of their pants and Crowley pushed Dean down and grabbed his legs so that his ass was hanging uncomfortably off the table -- good, make him beg for Crowley to be nice -- and pushed the tip of his cock between Dean’s cheeks, rutting against Dean’s cute little asshole.

“You were so _loving_ last night -- now you're so _mean_ to me.” Dean teased, faking a hurt voice. It was a fun game to play and he knew Crowley liked to assert himself, to be boss, to claim _fucking_ _dominance_.

“You were such a little _cunt_ at the meeting -- I saw how _cocky_ you were -- _how you winked at that bitch Cassidy_ ,” He growled darkly and pushed himself into Dean -- feeling his legs tremble at the sudden intrusion. “I knew you would be stretched still from last night you little _slut_. You like it when daddy’s rough with you -- you like the attention.” And Dean blushed furiously at that because yeah -- _fuck yeah_ \-- Crowley was right Dean did like the attention. Even after that embarrassing meeting when Crowley claimed him in front of all of his new coworkers, Dean realized it was what he really wanted. Crowley was possessive, rude and rough around the edges, and completely _enthralled_ with Dean. The young man found himself in love being the boss’s favorite _pet_. Crowley adjusted Dean’s legs to lay across his own shoulders and he started slamming into him relentlessly. He wanted Dean to feel this for days -- he wouldn’t heal him this time -- make sure he thought of Crowley every time he sat down for the next week. Dean could hear himself making the most _filthy_ noises, unable to control himself, feeling like the whore Crowley called him under his breath. _God he hoped the room was sound proof_.

Crowley felt his toes curl and he knew he was about to cum. He growled for Dean to touch himself, holding his hips in place while still slamming into him -- burying himself to the hilt -- loving how Dean screamed _oh daddy_ as he came. When he felt Dean’s ass spasm around his rock hard cock he lost it -- spilling cum deep into his pretty boy’s ass and groaning wildly.

They caught their breath still attached to one another, Dean turning into a pile of mush on the table and Crowley couldn't help but stare fondly from above. He hated himself but he couldn't help but clean Dean up, who muttered thanks in his dreamy sleepy state. He healed him too, just in case, the threat is more fun than the reality.

Dean’s legs were still wobbly and he almost fell over but Crowley reached out and steadied him.

“ _Honey_ . . .” Crowley began uneasy, realizing what he agreed to in the heat of the moment, “what did I agree to earlier?” Dean laughed and patted Crowley on the arm patronizingly.

“Hmm . . .” he couldn't contain his smile and it made Crowley want to shove him back down on the table, “I want to be able to ask you to do a favor down the line. I’m not sure what yet but I want you to give me an IOU.” A moment of silence while they both contemplated what that might be.

“That’s . . . such a _bad_ deal on my part.” The mood was light; Dean smiled sweetly and Crowley wanted to pull him closer.

“Are you sure you don't just want me to take care of Kent for you?” Dean raised his eyebrows in surprise at the demon, who smiled wickedly.

“How did you . . . ?”

“Darling, one thing you would do well to remember is that I have eyes and ears everywhere and I do mean _everywhere_.” Crowley buttoned Dean’s shirt, taking care to straighten out wrinkles and even fixed his tie for him. Dean stood very still for him to work and couldn't help but blush because it felt intimate. Crowley's hands working up his chest to his collar, his fingers just barely grazing Dean's collar bone. When he finished he patted Dean and then the two of them were blushing like idiots on a first date even though they had fucked just minutes before.

They finished dressing and Crowley made for the door. "Well . . . Good first day, Winchester. Keep up the good work and before you know it you'll be my _partner_ ,” and Dean’s eyes went wide and Crowley felt good at what he said so he winked one last time and left on that note.

It was only until he was halfway down the hall when the realization of what he just said hit him.

 _"Fuck._ I meant partner in crime -- not like, _boyfriend_. _Shit. Fuck._ What's wrong with me?!"

And Dean, still standing in the room where Crowley left him, realized he didn't know what Crowley meant -- romantically or professionally -- but he now knew how _very badly_ he wanted either. Castiel was the furthest thing in his mind.

Time may heal all wounds but a new rich powerful boyfriend sure helps too.

 

 

**Notes for the Chapter:**

> I was so disappointed that I didn't get this finished a half hour earlier. If I had I would have published this chapter on my birthday! I turned 25 yesterday! Whoohoo! (Sorry I'm still excited).
> 
> Hope the chapter was up to par! Love comments/kudos! It makes my day!
> 
> I'm still taking requests if anyone's interested! I haven't seen last night's episode but I heard it was a doozy! Message me at http://vulcanpride.tumblr.com/


	9. Hello, My Treacherous Friend

**Summary for the Chapter:**

> The next month wasn't as easy as Dean's first day.

The next month at work wasn’t as easy as Dean’s first day. Sitting alone in the company dining room working quietly over lunch, he no longer felt completely like a fish out of water. He was still fresh to the others -- still interesting to his co workers making him a target for practical jokes. Last week he had to run home and change clothes because somebody had a fire trap cleverly set up outside his office, which he set off trying to enter the damn office, and it burned most of his suit jacket and shirt to a crisp. His natural agility and speed saved most of his body and face. It had been a very bad day.

Dean would feel better if he had someone to talk to about it, someone to connect with, but he mostly spent his time talking to Ruby and she was busy with a thousand things every single day. Half of their conversations were over a brisk walk to grab coffee and a cigarette before she had to literally run up the stairs back to her office. Ruby handled recruitment, hiring and training but a big part of her job was to put out fires with new demon employees. Magical deals can go awry -- especially with demons. They’re mischievous by nature, _little pricks_ , and a little bit of torture here and there is inevitable.

But what really bothered Dean was the fact that Crowley practically disappeared from sight. It was obvious that something happened between them after they fucked the last time -- that Crowley had said something that made him feel awkward. He was shutting Dean out . . .  he needed time alone . . . or maybe the demon had just lost interest and moved on. Perhaps he wasn’t avoiding Dean at all but rather just didn’t feel like Dean was worth the time. Dean shook the idea off before taking a sip of his coffee to calm his anxiety. He tries to bury himself in his work. Whatever the reason why Crowley disappeared, it was best to just keep working hard, keep clean of drama, and to let the boss have his space. Not like Crowley would see Dean _anyway_. Dean tried to get two separate meetings with his boss to go over _business_ but Lilith laughed heartedly both times and shooed him away. It was infuriating. And even more infuriating is that Kent and his group of idiots saw it happen, and they teased Dean about it until they were blue in the face.

“Better watch out for the dog catcher, Dean-O. They’re looking for abandoned _filthy_ mutts like you.”

“Did daddy step out for a pack of cigarettes, _sweetheart_? Waiting for him to come back?”

“I’m sure it’s you and not him, baby. I’m sure you’re just damaged goods.”

Everyone here either sucked up to him or openly hated him; there was no in between. Dean had so far received 28 threats from various employees -- almost one a day for each day he’s been at the company (and yes he was keeping count). Sometimes people would just lean in close from behind Dean and whisper something nasty that they’d do to him if he ever screw them over. One time Dean had a note shoved to him during a meeting that depicted stick figures of the whole executive team defacing him with a gangbang. Dean tried hard not to let it bother him but without anyone to share the frustrations with he felt depressed. He wished Sam would talk to him; he was increasingly dismayed that his brother was also avoiding him. The last time he stopped by Sam’s apartment a beautiful woman answered, some brunette babe named Sarah, who told Dean that Sam had left early that morning and she didn’t know when he’d be back. She told him she would for sure give him the message and how odd was it that Sam didn’t mention he had a brother. Dean left feeling more hurt than before.

It didn’t matter though -- if Sam wasn’t going to answer the 100 calls Dean had sent his way then so beit. Dean was done being weighed down and outshined by his younger brother. Sam always had it better -- which is what Dean wanted, sort of, (he basically raised Sam with the help of their uncle Bobby) -- but Dean didn’t like that Sam was always better at everything without even trying . . . at school, at work, in relationships . . . Dean couldn’t even keep his long term boyfriend. Even _Castiel_ preferred Sam to Dean in the end. Dean felt like garbage. He abandoned the people who cared about him, who now won’t talk to him, and he wasn’t getting anywhere with his new job.

It turns out everyday families aren’t as willing to give their soul to Hell because of the reputation that several major employees -- most notably Crowley-- have made for themselves. Dean hadn’t made a single sale and his big “let’s make ourselves more available to the public” plan was a bit harder to implement than he had realized. The self loathing he fought so hard to keep at bay all these years came crawling back and he could feel it in the pit of his stomach. Dean rubbed his face tiredly. He didn’t sleep well the previous night, plagued with nightmares about falling down from the sky without anything -- or anyone -- to save him.

He didn’t see Crowley walk in but he could feel him. His hair stood on end and suddenly he felt flushed and hot to the touch. _Christ -- cool your jets, dumbass,_ he told himself. He pretended to read his article, hoping his flush wasn’t visible.

 

On the other side of the room Crowley was in the conundrum of either leaving awkwardly or facing Dean for the first time in a month. He had been avoiding him -- he didn’t like the way he felt around Dean -- he felt like a nervous teenager. He was never nervous and even when he had been a teenager he never acted like one before. He had lived for hundreds of years, been a leader in the wars against humanity for the bloodiest war in demon history, so why for fuck’s sake would he be nervous around Dean Winchester? Maybe it was because he felt comfortable around Dean and Crowley felt that way about so few people in this world. He walked up to a random employee and took their coffee, ignoring their pathetic sucking up, (“ _thank you, Mr. Crowley,_ ”) and made his way over to Dean casually. He would act like a man -- like the powerful demon he was -- he would face his problem head on like he always did and work through the . . . _feelings_.

"Hello, Winchester, hard at work I see," the demon spoke softly and sat down uninvited at Dean’s table. Dean didn't look up from his papers and muttered hello under his breath. It was a few moments of awkward silence -- Crowley watching Dean work, drumming his hands on the table, and waiting for Dean to say something more. When it was clear that he wasn't going to, Crowley took it upon himself to try for small talk.

"So . . ."

"Hmm?"

"How's life? How's Samantha?" Dean didn't like Crowley asking. Not only did he hit a sore spot but he was sure Crowley already knew and was just confirming the rumors. Sam and Dean were a big deal for a long time -- most people in the industry already knew them as a wonder duo before they started competing for the same higher-up positions. He was sure one of Crowley’s little minions had taken note that the brothers weren’t talking. It’s not like Crowley honestly cared.

"Not sure. Can’t get ahold of him." When Dean didn't elaborate Crowley signed deeply, obviously hoping for Dean to continue the conversation. Dean finally glanced up at his papers annoyed.

"What? You don’t really care, you’re just asking to ask. If you want to talk to me then talk. _You_ sat down so _you_ make the effort.

" _Testy_ . . ."

"Sorry, _sir_ , but if someone avoids _you_ for a month I’m sure you can understand if there’s a little _resentment_."

"Dean, I have been so busy--"

"Of course you have been."

" _Really_ ,"

"Sure, fine." Crowley tsked.

"I didn’t forget about you . . .” When Dean looked at Crowley disbelievingly, Crowley quickly added, “ _Doesn't mean I don't care_ . . . "

The words escaped him before he realized what he had actually said. He felt furious with himself for a moment, his treacherous body betraying him as his cheeks grew slightly pink. Dean gave him a funny look before leaning back in his chair and stretching. He didn't miss the way Crowley looked him up and down admiring the view. They both took a minute to collect their thoughts. Crowley was making an effort, it would be good to stay favorable with him. And although Dean wouldn’t admit it here and now, he couldn’t help but love getting attention from his strong and powerful demon boss . . . he didn’t want to ruin it.

His eyes scanned the room while he was lost in thought and he saw Kent a few tables back glaring daggers at him. It was only then that he realized that _all eyes_ were on them. He even caught eyes with Ruby, who was waiting in line for a coffee. She winked at him and threw him a thumbs up. Dean decided to use this moment to his advantage -- remind people that even though he and Crowley didn’t spend every minute together that he was still the favorite, and people better leave him the fuck alone. He changed tactics, suddenly smiling his pretty white smile, his charm suddenly radiating off of him. Crowley sensed the shift quickly. He glanced around and noticed what Dean had noticed several seconds before. People were watching.

Dean leaned forward and put a hand on Crowley's arm, just for a second, before relaxing in his chair. "Thanks . . . for asking about Sam. I tried calling him until I was blue in the face but he’s avoiding me. I even made an appointment with his secretary to see him on Friday but I have a feeling he's going to cancel. I wouldn't have expected him to be so upset that I left. It’s been very frustrating for me -- I don’t have anyone to talk to." He gave Crowley a very melancholy look, his eyes practically sparkling in the light. It did _not_ make Crowley feel bad about avoiding him.

"Hmm . . .” Crowley took a moment to think about how to phrase his next thought. He reached across the table and picked off fuzz from Dean’s shirt, then smoothed out the wrinkles near the collar. A very intimate act -- people would know that Dean was still his. “There have been rumors, Dean . . . of your brother and the youngest Milton --" but Crowley cut himself off when he saw the murderous look on Dean's face at the mention of the two. He changed courses abruptly. "Would you like to go to dinner with me tonight?" Surprise landed on Dean's face and the young man laughed. He gave Crowley a pointedly stern look and shrugged his shoulders.

"I don't know. If we go out tonight then will I not see you for _another_ month?" Crowley winced at the words. He felt so immature by his actions.

"Only if you don't want to, love." They sat in silence for a moment while Dean thought about it, genuinely not sure. He pulled out the newspaper he had read that morning from under his stack of papers. Opening up the business section he threw it in Crowley's direction.

"You _sure_ you’re available?" On the front page of the Business section there was a picture of Crowley and a curvy, buxom brunette exiting the opera building on Sunday night. The two were hand in hand smiling and laughing, unaware of their photo being taken in the darkness.

"What does _this_ have to do with business?" He tsked and tucked the paper into his suit jacket pocket. _Someone_ would be fired for this -- Crowley was obviously pissed.

" _Well it's important_! We could have a queen of Hell! What will that mean for our stock prices?" Dean mocked the article. He didn't seem angry but he wasn't going to just let it go, the demon was sure.

"The media will make something out of nothing. I assure you that evening was _completely_ harmless," he smiled sweetly which just made him look more guilty. Dean raised an eyebrow.

"So you didn't take her back to your place and rock her world?"

"Good god, _no_." Dean scoffed like he didn't believe him. " _I didn't_."

"Who was she then?" This had started as teasing but Dean was obviously upset now and Crowley didn’t have time for the invasions into his personal life or for a public row.

" _None_ of your business." And the matter seemed closed, finite. Something in Crowley's voice was warning, telling Dean to stay away. The young man sighed, deeply annoyed that Crowley refused to let him in.

"I don't know about dinner, _boss_." He began, softly, an edge to his voice, "I want the main course -- not just an appetizer." Crowley made to get up, frustrated by the conversation and frustrated with Dean. Everyone turned and everyone saw.

"I don’t have time for this. I'll see you _after_ our meeting, Winchester." His exit was so quick that Dean didn’t even have a chance to respond or take back what he said. He made the mistake of glancing at Kent who was smiling and laughing with his moronic clique. Dean took a sharp intake of breath in anger and stuck his nose back into his work. He was determined not to leave embarrassed, or to look at Kent, who he could hear laughing meanly with his coworkers.

 

 The meeting that afternoon was agonizing. Dean nearly fell asleep during someone’s presentation, and Crowley felt the same way because he cut it off short and told the guy to go think about how to present an idea without killing half the room.

At first Dean and Crowley were still angry with each other, even childishly sitting on opposite ends of the table, trying to not making eye contact, but eventually little flirty glances were exchanged and their moods softened. Kent was talking about increasing productivity at some point and Dean made a small crude hand gesture to Crowley and Crowley laughed out loud. Kent saw the whole thing and was bitter for the remainder of the meeting.

When it was over, everyone shuffled out excited for the weekend. Dean stayed behind since Crowley had asked him to earlier. They both seemed lighter, happier, after flirting across the table during the meeting so Dean jumped at the opportunity for another round of seduction. He didn't want Crowley losing interest and making "friends" with another cute young blonde thing.

"What can I do for you, sir?" Dean batted his eyes and smiled widely, but Crowley didn't get a chance to answer because Alastair slithered into the room.

"Are you . . . indisposed?" He asked glancing down at Dean. Crowley acted like he didn’t hear him, smiling robotically.

"Alastair, _old chum_ , I haven't seen you in ages! Have you killed anyone lately?" Crowley's mannerisms seemed off, like he was trying for nice but struggling to keep cool. Dean noticed it quickly but Alastair either didn't care or didn't seem to notice.

"Oh goodness no, I have people to do that for me." His tone was casual, and more frightening to Dean, he seemed truthful. Does he kill often . . .? "I see that you've made yourself _cozy_ with the Winchester boy." Crowley glared warningly at him. He took a minute to respond, tapping his fingers on the desk annoyed.

"Snagged him from under the Milton's. Thought you would be _jealous_." He regarded Alastair closely. “Speaking of _cozy_ your daughter came to see me recently.” Alastair laughed an ugly laugh, his voice echoing in the large room making Dean cringe.

“So I’ve heard. You taught her a fine lesson in negotiating,” he appeared uncaring, impassive. Crowley looked disappointed. "It was time for her to learn. She's spoiled -- thinks she will always get her way." He turned to Dean suddenly, his eyes glowing excitedly. "Ah, Mr. Winchester, how are you?" Dean looked to Crowley for a moment, unsure how to answer, but Crowley was watching Alastair closely and did not see.

"Fine thanks . . . ."

"You look so much like your mother, you know . . ." Dean shifted uncomfortably under Alastair’s gaze.

"I know I have her--"

"Her eyes. You have her beautiful eyes." Dean did not like the way Alastair said that. It sent chills up his spine. "I hope you haven't been spending too much time with Crowley here. He's a bad influence you know."

"I know he is," Dean took step closer to Crowley, closer to safety.

“You know, Dean. If you came to work for me as a . . . private agent, I could outmatch _anything_ Crowley offers you. Anything. I could teach you things you haven't even dreamed of.” Dean visibly shivered, though it wasn’t intentional. Alastair took it as rudeness, and made a sort of frustrated noise. “You should mind your manners in the presence of your elders.”

“I’m terribly sorry, _sir_ , but it’s just that the thought of working for you makes me feel ill.” Crowley laughed softly, stroking Dean lovingly on the arm as if to praise him.

Alastair had a funny look on his face that made him look demented. Dean wasn't sure if he had gone too far, if the bastard would snap him in half right here and now. He took a moment to respond, visibly collecting himself. It was the most uncomfortable few moments in Deans young life.

"Well then . . . I'll leave you two to your . . . Work." He made to leave but before exiting the door he turned around like he had just remembered something to say. Dean was sure it was an act -- rehearsed. He doubted Alastair came in for a friendly chat.

"I do hope to see you at the _retreat_ next month. We haven't seen you in years, Fergus. The others are worried you're getting soft in your old age . . ." He smirked and left without another word. Crowley looked murderous. Dean waited several seconds to be sure Alastair was out of earshot before asking questions.

“A retreat? Why is that important to him?”

“It’s a . . . get together for all the powerful demons and gods who fought in the great war.” He looked away from Dean, not wanting to go into it further. Dean let it go. He wanted other information.

"How do you know him?" Dean looked at Crowley seriously. Crowley took a few moments to answer, mulling it over while he pretended to fix Dean’s shirt.

"When I was very young and foolish I made a deal with him. It's haunted me every day since. I _hate_ the bloody bastard . . . but he’s technically my partner for the business."

“Your _partner_?!”

“Yes, he _technically_ owns half the company but he just rakes in the profits -- I do all the work, I’m in charge around here.” He said it like he was trying to convince more than just Dean. Dean thought for a moment, not sure how to phrase everything he wanted to say.

"He cornered me on my first day here. He looked like he wanted to eat me alive . . .” Dean left out the part about the nightmares he had been having. At first he wasn’t sure who the dark shadowy figure was -- looking at him from above with a thick blade in his hand and an evil smile on his face -- but now he was sure it was Alastair. Something about the man scared Dean to his core so profusely that he invaded Dean’s dreams. Crowley looked very serious for a moment at Dean, putting an arm back around him and patting his back.

"Don't let yourself be alone with him again. He had an unhealthy obsession with your parents and made them . . . very uncomfortable as well . . . " Dean was about to prod further, incredibly interested as he knew very little about his parents, but suddenly Crowley made to stand up and got his things together to leave. "So dinner . . . ?" Dean thought about it for a moment, sizing Crowley up and down, (his gaze unknowingly making the demon uncomfortable). "

Sure, _Fergus_." Crowley pinned Dean to the wall in the blink of an eye -- the demon’s hand to his throat.

"Don't you _dare_ repeat that to another soul." He looked serious, but Dean couldn't help but laugh.

" _No one_ knows your first name?"

"No one _important_. Not even _Lilith_ so you keep that to yourself, Winchester!"

Dean laughed, and with a flash of his pretty white teeth he said, " _We'll see_. Maybe if you show me a good time tonight I'll keep your secret, _Fergus_.”

 

 

**Notes for the Chapter:**

> Sorry this took me so long to update! I had lots of things going on at work -- and this chapter turned out way too long so I had to cut it into three chapters! So that means I have two more chapters almost finished after this one so just hold on a little longer. :)
> 
> Thanks to everybody for the comments/kudos and show of support! I woke up this morning to a lovely message in my tumblr inbox and it really brightens my day!! 
> 
> Anyone who has sent me a request on Tumblr: I'm working on it! Work has me so busy (and I also have a fiance and a giant dog that take up a lot of my time) so just know I haven't forgotten about you!
> 
> Find me at http://vulcanpride.tumblr.com


	10. Where is My Mind?

**Summary for the Chapter:**

> Dean and Crowley have dinner and sexy times commence. :)

**Notes for the Chapter:**

> TW: There is a sex scene this chapter and it contains fisting! I realize that's not everyone's thing so I wanted to give a heads up. If you skip this chapter you'll miss a little bit of fluff and fun but no major plot points! Lol that'll be next chapter!
> 
> Comments/kudos are always appreciated! <3 (Sorry for typos! It's late!!).

Dean arrived at Crowley's place a little early. He wanted to avoid Friday night street traffic and maybe catch the demon off guard. Entering the building and ignoring the doorman’s unsettling stare, he quickly walked to the elevators and rang Crowley’s phone to be let up to his condo. The demon did not answer but the elevator doors opened anyway and Dean was quickly on his way up.

Dean knocked on the front door and Benny answered. He wasn’t wearing the suit Dean had seen him in before -- instead in a casual set of dark jeans and a burgundy long sleeve t-shirt and a black apron speckled in bleach stains. Dean awkwardly said hello, a flush quickly staining his cheeks, and followed Benny inside. Benny pointed Dean in the right direction before going back to scrubbing the hardwood floors. Dean couldn’t help but stare for a moment at Benny bent over -- working hard at his job, his tight jeans showing off his firm round ass, and his back muscles rippling through his shirt -- before realizing what he was doing, quickly exiting the room feeling awkward and a bit like a pervert.

He walked down the hall slowly, taking in small details that he missed his first (and so far only) night he had stayed over. He heard Crowley's husky voice laughing and talking to someone on the phone. Dean listened intently and he tried to make as little noise as possible to try and hear who he was talking to so sweetly.

"Yes, I got the care package you sent . . . Yes it was lovely . . . Oh did you now? How is she?" Dean cleared his throat when he entered the study so he would not surprise Crowley, who was sitting with his back to the door in a nice leather chair, a forgotten book laying next to him, but the demon had sensed him the moment he walked into the building and without looking he motioned for Dean to come in and sit down.

"Alright, I have to go my date is here. Yes . . . I will . . . You too.” He hung up.

“Your sister?” Crowley didn’t answer but gave the young man a warning look.

“Sorry, I’m just curious.”

Dean batted his eyelashes hoping it would do the trick but Crowley made it clear with his expression that Dean was treading on thin ice. He didn't ask any further questions now frustrated that Crowley was so private. He shivered in the drafty room and pulled his coat on tighter. Crowley made no move to get up, instead snapping his fingers to ignite flames in the fireplace which roared brilliantly. He turned to Dean and smiled. For the first time Dean had known him he looked tired.

"Where would you like to go to dinner? I have a reservation at a delectable Mediterranean place but I wasn’t sure what you were in the mood for."

"That sounds great -- we can go anywhere, really. I don't mind _staying in_ either." Crowley looked at Dean oddly.

"Would you cook?" He asked after a short pause. Something else seemed to be on his mind. Dean smiled and nodded politely.

"I told you I'm a _great_ cook. I can make some pretty mean burgers." Crowley searched Dean’s face for a moment and for some reason it made Dean blush embarrassed. Then he jumped up, motioning for Dean to follow.

"I'll come keep you company in the kitchen then, pet." 

 

Dean was happy to see Crowley much more at ease at home this time. He was surprised Crowley agreed because it was much more intimate than going to a restaurant. Crowley showed Dean around a little more this time -- showing off the indoor lap pool he had on the second floor of his condo and the small replica Irish Pub Crowley had built when he was “bored one weekend”. Dean loved up every minute of it because he was eager to learn more about the man behind the demon. He longed to talk about Crowley’s personal life, where he grew up, what it was like to see the world change, what it was like growing up in a world without technology, but he instead asked questions that would keep the mood light and keep Crowley talking. Dean finds one picture in the whole tour that might be called a family picture. All the pictures hanging in the living room and hallway are of Crowley with various celebrities, but on their way out of the study he catches a glance at a small picture of the same beautiful brunette that he saw in the newspaper. She has to be his sister. Weird how Crowley hasn't mentioned her -- how he keeps her private.

When they finally reached the kitchen Dean was surprised to see Benny cleaning the counter tops (he worked quickly) -- his clothes still showing off his very nice physique. Dean couldn’t help feel himself get a little hard at the sight. Crowley noticed this, smiling deviously, and pushed Dean out of the way to clasp a hand on Benny’s back.

“Benny, love, if you are finished we need the kitchen. Dean would like to cook dinner tonight.” Benny looked to Dean, searching him up and down with his gaze, before responding to his boss.

“He’s pretty and he cooks?” He winked at Dean, who couldn’t help the red rushing to his face. It was the accent. The southern drawl killed Dean. Crowley glanced between the two of them before pulling a $100 bill out of nowhere and offering it to Benny.

“Go flirt elsewhere. Don’t get yourself into trouble.” Benny took the bill and slowly untied his apron giving Dean a view. He handed it to Dean suggestively, crowding his space, and taking his time in letting go.

“I know whatever you make will be delicious, darlin’,” He smiled for the first time and Dean realized that Benny was a vampire too. He left with a hungry look on his face. It was several seconds of Dean trying to decipher what just happened. Crowley was near laughing out loud, trying to contain himself.

“You’re so hot and cold with me,” Dean said after a beat, “You’re territorial at work and have no problem telling people to keep their hands off of me there, but Benny was like,” Dean gestured to his chest and body, “ _all up on this_ and you don’t have a problem with that?” Crowley shrugged, nonplussed. He walked over to Dean, crowding his space like Benny had moments before, and slipped the apron over his head. He tied the strings at Dean’s waste, eager to touch him.

“Maybe we’ll have him join one of these days -- if you’re both good boys and listen to daddy. I know you want to, _you little slut_.” Dean adverted his gaze because Crowley was right -- he totally wanted Benny to throw him on the kitchen floor and have his way with him.

“ _Jerk_.” Dean teased.

“ _Bitch_.” Crowley grabbed him by the shirt, kissing him harshly before finding a seat to watch Dean work his magic in the kitchen.

After a few moments of scrounging around the cabinets Dean decides that pizza is the way to go; Crowley had the perfect ingredients for a quick BBQ chicken pizza that would knock his expensive Armani socks off. Dean set to work and Crowley sat at the little bar and stool area off across the counter. He watched Dean closely.

Dean every now and then would make a frustrated noise, like he couldn't find something or when the sauce burned just slightly. Crowley loved watching him work and he found himself wanting to participate. At one point the demon made the mistake of trying to help Dean find a pan but Dean nearly growled for Crowley to get out of his space.

"Sorry I'll just --" but Crowley couldn't finish because Dean put his hands on him and pushed him back around the counter to his seat.

"I need the whole kitchen when I cook . . ." He said a bit sheepishly later. It was Crowley’s house after all and he shouldn’t push him around like that.

"No it's alright. I like it when you . . . assert yourself." Crowley had a drink in his hand and one waiting for Dean on the counter. Dean’s eyes widened for a moment and then he smiled mischieviously darting his tongue out to taste his lips. Crowley’s eyes flickered to it.

“I thought you liked being the boss.”

“Sometimes, but I see your . . . _potential_.” They both looked at each other knowingly.

“Well then I’ll have to . . . show you what I’ve got.” He set the timer for the pizza which was now safely in the oven before leaning over the counter to kiss Crowley passionately. "We have an hour to kill before the pizza is done . . . "

"You've never said anything sexier," Crowley took Dean’s hand and pulled him into the living room.

Dean plopped himself down on the couch and spread his legs as an open invitation.

"Would you like something, dear?" he asked, playfully, moving to stand in front of Dean.

"I don't want to hear you talk." Dean’s voice was instinctively deeper, darker. It made Crowley weak in the knees. "I want you to get down on your knees and apologize to me for calling me a slut," unzipping his pants he pulled his already hardening cock out. " _Show me how_ much you like me. I'm tired of feeling underappreciated. Show me how much _you want it too_."

Dean wasn't sure if he went too far -- that maybe he touched a nerve because Crowley looked at him curiously, then without a word he did just as he was told. One of the most powerful men in New York got down on his knees in front of Dean Winchester to blow him.

Dean’s excitement showed; his cock was rock hard and leaking. Crowley made sure to make eye contact with Dean as he licked up Dean’s cock from the base all the way to the tip before taking the head into his mouth and sucking in earnest. Dean took a sharp intake of breath at the hot heat of Crowley’s mouth, his hands instinctively reaching out to rest on Crowley's short hair, encouraging the demon to keep going. Crowley bobbed his head up and down easily, _loving_ the way Dean couldn’t keep the moans from escaping his mouth. He made sure to pull back and wrap his extraordinarily long tongue around the sensitive part under the head of Dean's cock, making him squirm from the intensity of it all, before going back to a relaxing his jaw and deep throating.

Crowley could tell that Dean was close to cumming from the sweat glistening on his beautifully scrunched up face, breathing deeply with a bright blush on his cheeks. He suddenly became demanding -- pushing Crowley’s head down so his face was smashed up against Dean’s perfectly trimmed pubis, grinding his dick against the back of Crowley's throat, keeping him there for longer than humanly possible. Crowley pulled off suddenly and laughed teasingly when Dean protested the separation. The demon yanked Dean’s pants down further so that they were pulled around his ankles, restricting his movements but allowing Crowley to slip a finger in his little asshole. He stretched and pushed in another finger searching for that sweet spot deep inside his pretty pet. When he found it, Dean writhed and moaned, praising Crowley’s skilled fingers and suddenly begging for Crowley to take him in his mouth again -- and Crowley did -- and the feeling of being played with and the tight wetness of Crowley’s filthy mouth sent him over the edge. He came screaming with just a couple more pumps while Crowley sucked him dry.

Dean let out a breath of release, suddenly feeling tired and like his legs were made of jello, but Crowley wasn't done with him yet. His fingers still wrapped around his cock and his other hand buried deep inside him, Crowley pressed down harder on Dean’s sensitive prostate before scissoring and stretching him more in his post orgasm state. He had four lubed up fingers in Dean before the young man pushed him away, his eyes scrunching up tightly.

“It's too sensitive," he softly croaked out, and while Crowley slowed down he didn’t stop completely.

"Take deep breaths, work through it. Daddy wants to put in his whole hand, make your cute little arse tremble, I wanna make you see stars, baby." Dean wanted to do as he was told -- the idea sounded so hot and his cock hardened slightly from the thought. He tried to do as he said, taking deep breaths and holding his legs to give Crowley a better angle, but the buildup was slow and burning and his legs started to shake like he couldn't take it anymore. When Crowley was able to get his thumb in with the rest of his hand he slowly worked his fist into Dean, who had turned so brightly red, his eyes shone with tears.

" _It's so intense_ . . ."

"I know, honey, and it'll feel _so good_ for you. I want to see you stretched open, baby, then I wanna _fuck_ your loose hole, _fill you up_ with my cum," He stroked Dean’s cock slowly as he experimented with his fist, pumping it deeper, inside slowly so not to tear or hurt him. Dean was such a little slut -- he was so horny for Crowley that it didn’t take long for his cock to become fully hard again, his hips slightly rocking in tandem with Crowley’s fist. It wasn't long before they had a good rhythm and Dean was practically _fucking himself_ on Crowley's fist and arm. Crowley loved seeing Dean this stretched, loved watching Dean become a babbling incoherent mess, his own cock straining against his suit pants -- desperate for attention.

Pushing into him deeper, Crowley could feel the walls of Dean’s ass contract around his wrist and he knew Dean would burst soon. He slowly took out his hand, hearing a filthy wet pop when Dean was empty, and he replaced it suddenly with his long tongue. He licked the sensitive rim before shoving his tongue inside Dean’s loose hole, along with one finger deep enough to graze his prostate. The whole thing was so intense that Dean bucked involuntarily, nearly kicking Crowley in the face. Crowley pushed him down, making quick work of his own pants, before getting on top of Dean and aligning his thick cock to slam into him. He growled into Dean’s ear as he fucked him on the couch in earnest, eventually grabbing Dean's hips and picking him up slightly to thrust in harder. Dean was an incoherent mess, both of his orgasms were so intense he didn’t believe he could cum again, but Crowley pounded so hard and fast into his ass, grinding mercilessly against his overly sensitive prostate, that after just a few minutes Dean couldn’t help but beg his daddy to cum one more time. Crowley emitted a low growl and wrapped his hands around his baby’s cock.

It just took a couple seconds of jerking Dean off before the young man came screaming Crowley's name, thrashing frantically while his ass tightened around Crowley's thick cock. The demon followed shortly after, filling Dean’s ass with cum like he promised, pulling out quickly afterward. Both men were breathing heavily but Dean looked as if he would in any minute pass out -- Crowley watched him through hooded lids as Dean tried to compose himself. 

“Spread your ass for me, honey,” Dean didn't open his eyes but did as he was told, pulling his legs closer to his chest and holding his ass open for Crowley to see. The demon pushed his cock just past the rim before pulling back out again, watching in ecstasy as cum dripped lazily out of Dean’s loose ass. Dean looked like a gorgeous mess -- sprawled out on the couch catching his breath, flushed from sex -- letting Crowley do what he wanted with him. Crowley soaked up the sight. Dean was _beautiful_.

He got up to go get his darling a drink of water. Dean looked like he needed it. He definitely deserved it. Dean drank two entire glasses of water before laying back down on the couch, not caring that cum was dripping out of his ass onto a couch probably worth more than his car.

Crowley spent a few minutes making sure he didn’t rough Dean up too much, petting him lovingly on the head when he was finished before opting to find something to put on the TV. A little background distraction while they would eat dinner, which should be done soon. Crowley’s back was turned to Dean while he rifled through his movies and suddenly he heard Dean make a small gasp.

“Something wrong?” The demon eyed Dean worriedly.

“You . . . you have a tattoo!” Crowley flushed suddenly, for some reason oddly embarrassed.

“You're _so quick_ on the uptake, love.” he said dripping with sarcasm. Crowley did indeed have a large tattoo on his back and though he would deny it later, he was offended Dean hadn’t noticed it before.

“I'm just surprised is all,” Dean looked high -- his eyes were glazed and his speech was slightly slurred. He must be exhausted from sex. The demon lost the small bit of anger he felt. Dean was too endearing when he was sleepy.

“You didn’t notice before?” He tilted his head curiously, examining him while he answered. Dean, slightly flustered, hurriedly gave several explanations.

“In the office you didn’t take off your clothes so I didn't see it then. And that first time we  -- well -- I mean -- I _passed out_ right after sex and you were on top. I'm usually a bit distracted with the mind-blowing sex and . . . and I’m always, you know . . . _under_ you.”

“Yes, yes you are . . .” The demon smiled sweetly as he thought of just that. He loved seeing Dean sprawled out under him, letting Crowley shove his cock into him until he was buried to the hilt.

“What made you get a tattoo?” Dean asked suddenly, looking to Crowley genuinely interested. Crowley didn't miss a beat, continuing his search for the perfect movie.

“Tattoos are fun, Dean. I’ve always liked them. I had tons of them when I was human . . . When you're a demon it’s great because it’s an easy fix if you get a bad tattoo. Want to change it up? Easy -- go get a new meat suit.” Dean furrowed his brow and suddenly looked much more awake than he did moments before.

“Yeah . . .  except you take someone's body _without their consent_.” He looked stern, like he found the idea incredibly distasteful. Crowley scoffed.

“Bullcock! We mostly _don't_ actually.”

“Then how do you--?”

“ _Sometimes . . ._ " Crowley cut him off,  ". . . we make it into a deal. This poor bastard that I’m currently occupying -- we made a deal for some stupid thing he wanted and part of my pay was that I take his skin when he died. There's a lot of people who don't want to do that though so _mostly_   we get them from coma patients. It's a nice program I started a while back with a few greedy doctors. We help the doctors because we can communicate with their patients, if they are not brain dead that is, and if they are a _vegetable_ then the hospital gets a small donation check and a demon gets a new body. It's a win-win for everyone involved.”

“That's . . . such a good idea.” Dean looked slightly disgusted but impressed nonetheless.

“I saw a resource and a need so I started the market. The beauty of capitalism.” Crowley pulled a cigar out of no where and lit it. He offered one to Dean who declined still deep in thought.

“It works so well . . .” Crowley handed a few movies to Dean, who took them without looking at them.

“You see Dean, life is meant to be mixed and integrated. People don’t live in a vacuum -- we have to live with each other on this messy planet. Take New York City for example: there are thousands of people doing thousands of different things every day -- crime, business, sex orgies -- but in the end the city remains in tact because we have a sort of organized chaotic system. It works for us -- and while there will always be  _some_ people break the rules and try to ruin it for other people,  _most_ people try and stay out of each other's way.  _That's_ why it's so silly to be fighting with Heaven. We can get so much work done if we work together! Imagine how quickly Heaven and Hell would expand if we weren't so busy trying to knock each other down!” The demon sat back happily, confused by the scoff he heard escape Dean.

“Never thought I would hear a demon preach anti war, I thought that was your guys’ thing,” He seized Crowley up and down like it was the first time he had really looked closely at him. Crowley did the same to Dean.

“Do you assume _all_ demons are heartless creatures that only want to torture, maim, and destroy?” Dean didn’t miss a beat.

“Well -- yeah,” Crowley shrugged.

“Well, you're racist, Dean.”

“Huh . . .” Dean looked serious, deep in thought. He seemed greatly dismayed by the notion.

“Dean, demons and angels -- all monsters really -- are similar to humans in that we are all _different_. Personally, I enjoy organization -- I enjoy working toward a common goal,” His eyes twinkled in the dim light, his low voice smooth as silk, “ _That’s_ why I’ve been trying to merge with the Miltons for years. Imagine what we could accomplish if we all just worked together.”  He looked to Crowley incredulously.

“You’re _kidding_ me.”

“No, I’m not.”

“The Miltons _hate_ you . . .” Dean said after a beat. He wasn’t close with Castiel’s family per se but he had been around them enough to hear how they felt about demons -- and humans, actually -- the Miltons were kind of giant douchebags. They hated  _each other_  first and foremost and then just about everyone else.

“ _I know_ . . . An unfortunate incident with Raphael has left me unfavorable to the others . . .” Crowley looked away supposedly in shame but Dean saw a small smile had crept onto his lips.

“Which was . . . ?” Crowley laughed softly and thought about how to phrase his answer.

“Let’s just say that with Castiel’s father’s drinking problem the family business has been in trouble for a while -- you know that.” He turned to Dean to gage his response. Dean did know about Castiel and Raphael fighting over control of the company for several years (since their father had relapsed in his therapy). It was very hush hush -- very few people knew about it -- but that was about the extent of what he knew.

“Of course I know about Mr. Milton but honestly I don’t know much beyond what Castiel told me.” His mind drifted to Castiel. Dean wondered how he was doing; how he was holding up being the family’s strong front. He suddenly felt very sorry he never returned his phone calls. They could remain friends . . . couldn’t they? Didn’t he owe it to Castiel to stay close by in case he really needed someone? What if he was like Dean, with no one to talk to? Crowley did not notice Dean’s sudden drop into sadness -- too distracted with talking casually and enjoying his afterglow from earlier. He easily filled the silence.

“Well once upon a time I went and asked Raphael to work with us and he agreed but his demands were so . . . so _outrageous_ that I couldn’t help but teasing him instead. He has _no_ sense of humor, you know.” He smiled mischievously, and it made Dean smile back. “He hates me. Castiel hates me too . . . my little prank tarnished the Milton name. Not like their drunk of a father hasn’t already. Leaves his headstrong boys to their own destruction while he travels the world and remains constantly unavailable -- now that’s _really_ evil if you ask me." He downed the rest of his Craig and brought Dean's attention back to the movies he picked ( _Death To Smoochy, Fight Club, and Django)._

Of course Dean picked _Fight Club_. There was never another choice. The two scootched closer to each other on the couch to watch the movie and wait for dinner to be done.

**Notes for the Chapter:**

> Told you I would update soon! This chapter just needed a few more touches. The next few chapters are semi written -- if I take another month to update I deeply apologize in advance! Holidays are coming up and that's very busy for me at work so bear with me! :)


	11. Sam?

**Summary for the Chapter:**

> The very long waited next chapter . . . I truly apologize for taking so long (and there's not even porn in this chapter!) I hope for those of you who are still waiting and still reading that this is worth the wait. <3

  
Though the day had been warm from the sunshine, the night felt air crisp to Castiel’s skin and he shivered. He pulled his trench coat tighter and fixed the scarf he wore snugly around his neck. It was a recent addition given to him by Dean before -- before they broke up (it still hurt to think about it). He honestly believed, there wasn’t a doubt in his mind at the time, that Dean would realize his mistake and come back. However Dean did not come back and over a month went by without Castiel hearing a goddamn word. He didn’t even give the angel a chance to make everything alright again. He wouldn’t respond to Castiel's texts or calls . . . he even made a public appearance with -- _with_ _him_. To go to Masas with Crowley was an insult to Castiel personally. It disgusted him to see Dean-- _his human_ \-- with that demon. And they made the whole damn thing public too . . .

With a sigh, he briskly walked down Park Avenue towards his office. He glanced at his phone, noting the time, and became overwhelmed with the temptation to call Dean. He pushed the thought away as soon as it entered his mind. Nervously palming the phone in his trouser pocket, he stopped before entering the office to catch his breath and took a moment to look at the building closely, feeling as if it was the first time he had ever seen it. The angel used to feel so at home here while working with his father and his brothers, during what Castiel refers to (in his mind) as the “golden years”. The Miltons made a name for themselves here -- though not that they didn't already have a strong family name. They were made up of generals, famous soldiers, and strong leaders that fought brilliantly alongside God in the magical crusades. The war was the bloodiest that mankind had ever seen and the death toll for demons and angels alike was astounding, but their victory led the Miltons and other magicals like them to enormous success in the 21st century. Even if _Heaven's Little Angels_ went under, the family's wealth and resources were vast and unlimiting, much like the dark starry sky Castiel stood beneath contemplating and waiting. . .

‘ _Biding time, Castiel_?’ He could almost hear his father’s voice speak too him, an echo of a distant memory. No one had heard from Mr. Milton in over a year. Castiel had to assume he was dead or wanted nothing to do with the family. Or perhaps he had finally drank himself to death -- that's how Anna said he would go. Or maybe he just went on a permanent vacation, (' _that stupid prick,'_  Castiel thinks) as that was something he always joked about doing. Castiel prefers that his father never returns as the damage done is irreversible. It would be so much worse, Castiel thinks, if he just shows up out of the blue one day like nothing ever happened. _That's how he'll do it, that bastard_. And then it would be a sickening game of who can jump at father's heels the fastest. Disappearing without a trace and abandoning his children, all of his responsibilities left a power vacuum that is overwhelming to fill. Castiel's brothers argued for months on who would take over the business while his one and only sister snorted so much angel dust that she's been in a psychiatric ward for over 7 months now. Castiel almost can’t seem to bear it and feels like he is slowly losing his mind. With Gabe gone and Anna coked out of her mind, and now with Dean gone . . . Castiel feels as if he has lost all of his allies. He felt like all he did was constantly argue with his brothers over this past year, who at the time of his father’s disappearance seemed _eager_ for the young blue eyed angel to be the spokesperson and CEO. After all, his brother's explained, who wouldn't sell their soul for a look into those dreamy eyes? However when Castiel actually had ideas to implement, when he actually tried to work hard at his job and be the best he could be for the family, his brothers protested every step of the way. It was so incredibly infuriating that coupled with losing Dean and Sam behaving strangely, Castiel had no idea what to do. He sighed feeling very much alone.

He looked across the street at _Hell Inc._ wondering if Dean had to stay late that night too. _Stop it_ , he thought to himself. He tried to push the thought of Dean away from his mind again. It hurt him to think about Dean (he missed him so much), but also because Castiel felt so ashamed about that night with Sam . . . how could he not just come clean with Dean? Why did he have to push him away? He didn’t tell Dean when he had the chance, and though something didn't feel right about that night he never -- Castiel never imagined that Sam would . . . It doesn't matter anymore, the angel thinks. Sam will answer Castiel's questions and then their partnership would end. He could confront the youngest Winchester now that he finally had proof (even if it was just a grainy three second shot of the door to Heaven’s safe). He could take Sam easily if push came to shove, though it is not necessarily a fair fight to pin an angel against a human, but he had to take control of his company again. Sam was . . . not himself lately, and he exercised too much power these days. Raphael agreed just a few hours ago that it was time that Castiel "took care of business". When the young angel showed the brother the video of Sam breaking into their most treasured safe, Raphael told Castiel it was time to “Get the little boy out of the big boy chair.”

So through the golden arches he went, into the decadently decorated reception area. He ignored the hellos thrown to him by the ever smiling staff and walked quickly down the marbled floor hallway, trying to ignore his family’s haunting portrait hanging eerily over the grand fireplace. Michael and Lucifer, the two oldest (' _and favorites'_ , Castiel’s subconscious chimes in), side by side their father, looking particularly disdainful.

Michael and Lucifer had been in and out of care facilities, much like their alcoholic father, but instead the two eldest sons had a particularly hard time finding bodies to house their substantial powers. Michael had one meat suit for several decades now, the longest he's been able to keep in two centuries, but it was finally falling apart and it made him look like a walking corpse. The last few years he's been seen less and less publicly, no doubt due to the sheer embarrassment of being one of the most powerful creatures to walk the face of the earth, reduced to decay and rotting flesh. This is a fate destined for weak _humans_ , not Angels of the Lord. Lucifer was a bit different from his brother Michael, to say the least. He didn't mind walking around town in a corpse-like body. He actually enjoyed the panic it caused wherever he roamed. Though even then, a rotting meat suit is like a crippling disease for magicals. Soon the vessel is so badly damaged and broken that even Lucifer cannot enjoy it. How much easier would it be if they were demons, who fit into the tiny space of human flesh so efficiently.

Below them in the painting stood Raphael and Gabriel, one stoic and the other smiling heartedly, looking like complete opposites. Gabriel left the family business as soon as their father had taken one step out the door. He had always wanted to go live a simple life with his fiancé Kate, and that is what he was doing. Castiel receives beautiful postcards from his brother while he travels the world, but he still misses him greatly. If felt like Gabriel was Castiel's last true ally in the family. Raphael is the only one left to help run the family business but they are seldom in agreement, and it is putting a strain on their once brotherly relationship. Raphael is very conservative and he likes keeping the . . . old ways. The retreat that "everyone loves," the retreat to “keep morale up,” Raphael would tell Castiel one late evening over whisky, is his idea. “Play the game,” the elder brother coaxed so sweetly, and Castiel’s protests died that evening with his last sip. But Castiel knows better. He’s seen the look in his brother's eye when he thinks no one is looking. Even as he stares at the massive portrait, he sees that same menacing stare and a familiar knot forms in the pit of his stomach.

In the front of the painting is a youthful Castiel, looking small and fragile compared to his older brothers, with messy hair and big sorrowful blue eyes. His fiery redheaded sister was poised perfectly to his side; her freckles and green eyes seeming to pop on the oil canvas. ' _Oh Anna,_ ' Castiel's heart aches. No one has the heart to take the painting down, though it certainly wasn't his family any loner. Castiel did his best to ignore the sick sensation he felt from his father’s painted eyes, boring into him, reminding him, ‘ _I’m always watching, Castiel_ . . . ’

He made his way to the golden elevator and pressed the button for the top floor. ' _There’s no other way around this.'_  Castiel would go to his office first to prepare and to get his angel blade. He would record a message on his computer . . . just in case things go awry.

As soon as new exits the elevator, however, he senses it: a familiar buzz of electricity in the air that makes his heart race. He prays silently for a quick moment that he’s wrong, but when he sees his office door open and the light is on, he knows that this will not end well. Making a split second decision, he texts Dean before tucking his phone inside of his coat pocket.

Castiel hesitantly walks into the room surveying his surroundings and keeping the door open. Sam glanced up from his papers, sitting at Castiel's desk so comfortably anyone would think he owned the place. He smiled widely, a grin not unlike the cheshire cat in Lewis Carroll's book. His once long and messy hair was slicked back with gel, giving him a slick professional appearance, and he wore a yellow carnation on his jacket lapel that Castiel had not seen him wear before. Sam looks at Castiel up and down, sizing him up before speaking, a ghost of a smile appearing on his handsome face. ‘ _He must know_ . . .’

“Castiel! What can I do you for you?" the young Winchster asks as if he doe not already know, but Castiel does not answer. His blue eyes starred deeply at Sam as he seemed to be examining -- scanning. Sam didn't seem to be bothered one bit. He stretched his arms up toward the ceiling and yawned. “Not for nothing, Cas, but the last time you looked at me like that I got laid.” He winked and smiled wolfishly at the angel, who furrowed his brow looking crestfallen.

Castiel willed his voice to sound more confident then he felt. “I know . . . I know you’ve been taking souls.”

There was the smallest beat of silence before the young Winchester laughed loudly and heartedly. Wiping his eyes, he gestured for Castiel to sit but the angel did not.

“Castiel -- Cas, please. You know I wouldn’t do anything to jeopardize the company -- to jeopardize what we have built together!” he paused to examine the angel with hungry eyes “-- our relationship,” he smiled again but it lingered too long, turning lecherous and cruel. Castiel’s stomach turned into a tight knot.

“Stop! I'll never forgive myself for that night. I-- I've had feelings in the past but that night--”

“Was amazing. I wish you would let me tell Dean! He would be so happy for us -- really! I'm sure he wouldn't mind at all.” It was so hard for Castiel to hear him speak so conversationally, like they may be talking about something pleasant such as the weather. Sam may have sounded genuine, but Castiel knew better. Something dark had slipped inside Sam and he had been too blind and too distracted to see it before.

"What has happened to you? Why are you doing this?" He looked at Sam -- really looked at him closely, and the young Winchester smiled sweetly with a small shrug to his shoulders.

“I don't like the game, Castiel.” He stood up and walked over to the window, seemingly for a dramatic effect. Castiel watched him as the tall man sighed with a mock look of disdain. “I'm tired of playing by _human rules_. You know what I see when I look out of my office? When I look at all the _little people_ living their _little lives_ below us?” He looks to Castiel, eyes manically wide, "I see potential! Potential of what our lives could be if we just . . . _take_ what we want. But you know about that, don't you baby?”

It happened in the blink of an eye. Castiel punched Sam square in the jaw. The sound of crushing bones seemed to reverberate in the large office and Sam stumbled backward. He looked at Castiel with amusement in his eyes and with his own two hands, he pushed the bones back into place in a sick macabe fashion that couldn't be possible for a normal human.

“Oh YES, Castiel, why don't you tell me how you _really_ feel?” The two circle each other slowly, one person heated and the other taking pleasure in what was to come.

"I FEEL that you have your own personal agenda and I CAN'T let you do what you’re doing to the company! You can’t take the souls -- we have an obligation to uphold our deals--” Castiel takes a large step forward while Sam takes a large step back.

“And we _are_ upholding our deals, Castiel. 'Eternal paradise for the price of your soul!' that’s our slogan right? The souls I’m using are _perfectly_ fine. I’m keeping them safe--”

“Then why do you even need them? What are you even planning?” Sam hakes his head like Castiel is a child who misbehaves.

“The matter is closed, Castiel. Raphael is on board with this. You're either with us or against us.”

“But he-- As CEO, I have certain power and weight--” the angel begins but the tall man laughs cruelly. 

“Oh didn't I mention? I'm sure you're aware that Michael is in charge of your father’s estate in his absence, and in lieu of your recent failings, Raphael and I convinced him -- well . . . we _all_ think it's time you stepped down as CEO.” Sam looks to Castil like he feels sorry to break the news though Castiel can hear the amusement in his tone.

“How dare you--” the blue eyed angel began again but Sam puts a hand up to stop him.

"Oh Castiel! We thought you'd fight us about this. We need _strength_ right now, Castiel! We need _leadership,_ and you can't handle it! You can't even resist cheating on Dean!” Anger flaring, Castiel's eyes glowed a silver blue, and in a flash he was back at Sam’s side with his right hook, but Sam caught his fist and crushed it with one hand. Castiel fell to his knees in pain but Sam held on tight. “You've made a fool out of yourself. Again and again, and then you let Dean join our competitors -- like you couldn't make another _stupid_ move." He twists Castiel's arm and shakes his head in mock disappointment when the angel screams.

“You can't just--” Castiel groans, but his words are lost in another twist of his mangled hand.

“You don't understand. It’s already done.” He leaves Castiel panting on the floor, slicking his hair back after a quick fix of his tailored jacket. “Now I have a lot of work to do so if you could just . . . ” He waved his hand toward the door not bothering to meet Castiel's pleading gaze. Several moments of silence passed before he spoke again. “You’re still here, angelface?”

Castiel knew he couldn't back down. This might be his final stand, but this isn't something he can just let happen. He stands up, blood dripping down his arm, and sighs deeply. “I can't let you do this, brother. You have to be stopped.” Sam looked to Castiel like he truly was pathetic. With a snap of his fingers there was a slight crack and it all went dark for the angel.

**Notes for the Chapter:**

> Hey guys. Sorry it's been so long! Life is crazy isn't it? It goes by so fast and suddenly it's over a year later and I still haven't updated! Now I see why people work on novels for years… And goddamn I sure like to talk a lot in my stories. There's much more to come! My only regret is how slow I am! I have a tendency to say this almost every chapter but I have quite a bit written for the next few chapters sooo hopefully I can post those soon too. Thank you all so much for your kind comments and wonderful support! It is such a great confidence booster. Love you all! I have no intention of abandoning this story. I just apparently have a lot to say and sometimes it's hard to find time to write it. <3


	12. Baby, Lately I've Been Losing Sleep Dreaming About The Things We Could Be

Dean woke up disoriented, though he quickly realized he wasn't alone. In the darkly lit room, he found Crowley sitting right next to him and the previous night came rushing back. They had apparently fallen asleep during the movie and were too comfortable and tired to move but it greatly surprised Dean that Crowley, once again, did not wake him and tell him to go home. He had been so uncomfortable that first night that Dean felt like he had very much overstayed his welcome. It was surreal to find the demon asleep below him, snuggling on the couch. He gingerly moved Crowley's arm that pinned him down to the demon's chest and managed to climb off the couch without waking him. He grabbed Crowley's forgotten shirt laying on the floor, unsure of where his own clothes lay in the darkness, and dressed himself to go find the nearest restroom. He paused for a moment and watched the demon breathe in and out, sleeping just like a normal human person. His eyelids even fluttered as he snored. Dean couldn't help but find it endearing and wondered if he was dreaming.

Dean walked quietly out of the living room to the second door down the hall, and he discovered the most expensive restroom he had ever seen or stepped foot in. The heated marble flooring almost felt sinful as it warmed his cold bare feet, but no sooner than he had shut the door he heard Crowley yelling "NO!" before hearing a loud crash from the living room. Dean ran to the source, shirt askew, a sheet of sweat glistening from the panic.

Dean was relieved when he saw there was no intruder and that Crowley was still asleep. He had slipped down off the couch, flailing against something in his nightmare -- he must have managed to knock over his own expensive lamp. “No . . . Please . . . Leave them alone!” the demon pleaded with someone Dean couldn’t see. Dean had his share of night terrors in the past and felt sorry for Crowley. He carefully knelt down and stroked Crowley’s crown to gently wake him up.

“Hey . . . . Crowley . . . Crowley! Hey Fergus!” he finally bellowed, and in a matter of seconds he was thrown against the opposing wall, the wind knocked out of him, Crowley's eyes glowing red as his hands rested none too kindly around Dean's little neck, pressed harshly against the wall. He grabbed at Crowley's hands for purchase but his grip was so tight that Dean struggled to breathe.

It took Crowley a second to remember where he was and who was in front of him, but he immediately let go of Dean when the disorientation cleared and took a step back.

"Are you okay?! Did I hurt you?" His voice sounded weak from sleep, and Dean heard the worried concern -- he knew he didn't mean to hurt him. He felt shaky with his adrenaline rushing; he had almost been choked out.

"Yeah, I mean, a little. I'm fine, though, you just scared me is all. You were -- you were dreaming."

Crowley looked at Dean without blinking, apparently lost in thought. Dean suddenly wasn't sure if he should even be there.

“Sorry -- I should have -- I should go,” he said awkwardly and made to move toward the bathroom door again, severely disappointed when Crowley did not follow. On his way back out, still dressed in Crowley's shirt, he saw the demon sitting wearily on the sofa, his hands rubbing his tired eyes. The lights were on and Dean could finally see the time. It was close to 5 in the morning . . . the sun would rise soon.

He sheepishly waited for Crowley to acknowledge him. To look at him. It took longer than he had hoped, and Crowley looked at him curiously.

“Do you know where my clothes are?” He heard himself say nervously, but the demon didn't seem to hear him. Staring at the young man, completely lost in thought. It made Dean uncomfortable.

“Crowley --”

“Yes, sorry,” the demon said before Dean could ask again. Without getting up he snapped his fingers and Dean's clothes appeared on the coffee table in front of him.

“Thanks . . .” Dean made to grab his clothes but suddenly Crowley was at his side grabbing his stretched out arm gently.

“You -- I would -- you can . . .” He was looking up at Dean, his brown eyes looking glossy from sleep, struggling to find the right words. Dean eyed him curiously. He did not move away but he didn't help him either. Crowley sighed, closed his eyes for a second, and with more confidence said, ”I would like it if you stayed. The whole night. Please.” He looked at Dean, almost annoyed that he was forced to say it, and it made Dean smirk something awful.

"I would love to. I mean, not that I don't like walking home alone at 5 in the morning . . .”

"Nonsense, Benny would have driven you, but all the same I want you . . . Here." It lingered in the air. Crowley wanted Dean. He didn't want him to leave . . .

"I would love to." He said again for the assurance.

Crowley snapped his fingers again, the continuous play of the DVD menu switched off along with the tv and the lights. Crowley made a show of getting off the couch ("old bones" he croaked out) before leading Dean down the hallway to the top floor and Dean nearly skipped the whole way down the hall.

  

The next morning Dean found himself alone in Crowley's bed, the sun shining through the open windows disrupting his sleep. He never wanted to move from Crowley's bed again, it was so comfortable. He smelled food, however, and his stomach growled angrily, and he was forced to move.

He stretched for a few minutes before scavenging for clothes. He found a robe on the little table by the window and was excited to find that it had ‘Dean’ embroidered on the front.  
He examined it carefully noting that it was of the highest quality (of course) and to his surprise and amusement it had embroidered on the back ’ _property of F. Crowley_ ’. It should have angered Dean, he was his own man of course, but something about Crowley's possessiveness . . . It made him feel special and it made him feel wanted. He laughs at how short the robe is -- it just barely covers his ass, and he wonders if it was on purpose or if the demon had actually forgotten how tall Dean is. Dressed in his new robe, he made his way to the smell of breakfast coming from the kitchen.

When Dean entered the dining room Crowley was seated at the table comfortably, talking on his phone. He looked very relaxed and well rested with a cup of coffee in his hands, deep in conversation. He smiled at Dean, his eyes flickering to the robe but before either of them could acknowledge the other, Benny came bustling through the kitchen door with a tray of food.

"Sleeping beauty finally woke, huh?" Dean heard the drawl from across the room and was suddenly very aware of how naked he was under his very short robe. Benny had a plate of food in his hand that he was setting down in front of Crowley, but he looked seductively at Dean the entire time, licking his lips when his eyes examined Dean’s body eagerly. He can't help but notice how handsomely rugged he looks this morning with a tight fitted cream shirt that showed every ripple of muscle.

"Yeah, but no kiss from a prince," the words poured like honey before he could contain them, and Dean blushes brilliantly when he remembers that Crowley is sitting between them. He probably wouldn't appreciate Dean flirting with Benny, especially right where he could watch. Crowley said nothing but clicked off his phone watching them amused.

"Oh, it's never too late for that, darlin'." Benny took a few steps closer and Dean looked to Crowley but the demon seemed nonplussed by their flirtatious. "What're you havin' for breakfast, honey?"

When Benny was inches from Dean, he thought he might actually just reach out and grab him in for a kiss, but Benny reached out and fixed the collar on Dean's new plush robe instead. Before Dean could choke out a response, his heart rate thumping wildly, his cock suddenly very awake, Crowley finally coughed to make his presence known and Benny took a large step back.

"Just make him the same thing, Benny, he'll need his strength today." Benny nodded at Crowley before turning to Dean for one more look over his handsome frame and then left to bring Dean food. Crowley winked and motioned for the blond to come sit next to him at the table. He quickly wrapped an arm around Dean when he sat down, bringing him in for a kiss.

"If you're not careful there, you're in for a three way with a demon and a vampire." Crowley's hand traveled to Dean's thigh, and slowly slid up to graze the hem of his robe. It tickled and Dean blushed further.

"I-- I think I'd like that."

"I know. We know Benny would too. And he's been asking for a raise . . .” The twinkle in Crowley's eye gave him the most mischievous look.

So when Benny reentered the dining room with a tray of food for Dean, Dean couldn't help the ten shades of red he felt his face turn. When did he become such a little slut? Has it since he met Crowley? He can't contain himself around anyone these days! Anyone attractive that is . . .

“What do you want to do today?” Crowley asked breaking Dean’s line of thought.

“Hmm?” Dean had been distracted and he looked to the demon curiously. It was Crowley's turn to blush.

“I wasn't sure -- I was thinking we could do something -- together I mean.” Dean smiled his pearly white teeth at the demon, trying to turn on the charm.

“Even if we hang out here, I'll be happy just to spend the time with you.” And he meant it -- it came so easily for him to say, and Crowley felt something swell in his chest.

“How does a day at the beach sound? I hear Hawaii is nice this time of year . . .”

Crowley and Dean teleported to Hawaii about an hour after breakfast. Crowley borrowed his client’s place in Kauai and the two spent a lovely day relaxing in the sunshine without a care in the world. The beach house (which Dean considered a small mansion) was perched precariously on the side of a cliff, and it had a small trail leading to a private beach. The sun was shining and the water was crystal clear -- it felt amazing. They laid on the beach occasionally kissing, but mostly talking.

They only returned when Dean felt like he officially had enough sun, and Crowley wanted to be sure they made their dinner reservations in New York.

"Italian okay?" Crowley asked as they got into the back of his car, both showered and dressed after returning from the beach. Benny looked stoic and poised as ever in his driving suit and Dean flushed -- he couldn't help it.

“Yeah . . . Sounds great,” Dean heard himself say, but he was finally getting around to checking his phone since yesterday and was distracted. He had a text from Cas.

 _Please call me. I need help, Dean. I need you right now_.

He didn't know how to take the text. _That's right you need help_ , he thought spitefully, but he became overwhelmed with a sense of worry. He noticed Crowley trying to read the text message over his shoulder nonchalantly so he made it easy by just showing the demon before he put it away.

“Hmm . . . You might want to call him . . . See what he wants.” The demon doesn't look at Dean while he speaks, instead inspecting his cuff link on his sleeve.

“He's been calling me night and day since he saw us at the restaurant. I _know_ what he wants. He _can't have_ what he wants.” Dean doesn't want Crowley to think he will go back. He's enjoyed spending quality time with him, as a person, like a genuine real life person. No tricks, no work, no games. Whether or not they stay romantically involved, Dean feels a bond forming with Crowley and he senses that the demon feels it too. He chooses to just text Castiel back since the Angel texted him -- couldn't be that bad if he didn't call.

 _What's up? Are you okay_?

He tucks his phone in his pocket, making sure to set it to vibrate before doing so. When he's done, he looks to Crowley and sees a genuine smile. “Let's go, darling,” and the two happily step out of the car to the street for their date.

  
Just shy of two hours later, they are leaving the restaurant and the two lovers are in the heat of a debate. Their voices echo with their passion and it draws the attention of the surrounding pedestrians trying to enjoy the nice evening. Neither man is really angry, not yet anyway, but neither will back down to the other.

When they get in the back of the car they are so engrossed in their conversation that they do not give Benny any direction, like they've forgotten he's even there. Benny chooses to head to Crowley's apartment, and he closes the sound barrier as the two become louder with each point they make.

“You cannot tell me that she seemed interested in your proposition,” Dean huffed, his cheeks reddening slightly.

“No, but _pray tell me_ why it bothers you so much, dear? You seemed to like her quite a bit from where I was sitting,” the two had run into an acquaintance of Dean’s, and he unabashedly invited her and her husband to their table. Crowley didn't seem to mind at all at first, but his behavior at the end of dinner was outrageous.

Dean took a moment to answer. He could feel the tension rising and he didn't want to spoil what was otherwise a perfect day.

“Well, sir, she _could have been_ a new potential client but that's not possible now,” he spoke carefully but Crowley still scoffed feeling annoyed.

“Oh please, a woman like that? There's no reason to worry, love! She's a _bloody nobody_! Who cares? That's one person out of a billion, boyo. And besides, I thought she would have been interested to come home with us, and I thought _you_ would have been too, given the way you practically made out with her in front of me,” Dean blushed knowing very well that Crowley meant the way she hugged him, lingering too long, feeling his muscles through suit. He crossed his arms and legs, physically closing himself off.

“Her brother is one of the heads in the department of labor -- didn't you hear her mention her brother Johnny? I knew I recognized her. I met her several years ago at the Milton’s family barbecue--” Crowley made an incoherent sound as if the idea revolted him. His anger seemed to dissipate instantly.

“Good god, I can't imagine going to that willingly,” he seemed much less tense, maybe even realizing his mistake.

“It was pretty interesting . . .” Dean acknowledged. He looked to Crowley earnestly, realizing that the fight was suddenly over. “Has it ever worked to ask a lady during dinner in front of her husband to come home for a sloppy gangbang with your date and your driver?”

Crowley nodded his head amused, “I have never been turned down in the history of my proposals for gangbangs, thank you very much. You obviously messed up my groove, Dean Winchester. And besides, her husband was invited too.”

Dean laughed as if he didn't believe Crowley for a second, and he felt much more at ease. It felt good to know that Crowley is sensible, that he doesn't hold on to a fight. “I was trying to make a sale, boss.”

“I forget how good you are at your job, Winchester,” And then Crowley did something he hasn't done before -- he held Dean’s hand. Dean tried his hardest to contain the excited little butterflies jittering around in his stomach. He sighed in relief and turned to give Crowley a kiss.

When they arrived back at Crowley’s apartment, the two couldn't keep their hands off each other. Dean loved that he had this sort of effect on the demon, it seemed like he couldn't make a coherent sentence the minute Dean batted his eyes. The car ride home seemed agonizing and they couldn't help but start the fun early. They lost their suit jackets first, belts coming undone next, and finally Dean’s shirt too, leaving him in his suit pants and tight white undershirt.

Benny said nothing while he watched the two stumble into the building, hurrying toward the elevator door. They barely reached Crowley's apartment, just walking past the front door, and then suddenly Dean was pressed up against the wall with the demon biting his neck down to his chest. He pushed forward against him, rubbing their strained erections together which provoked a low groan from Crowley as he made quick work of their trousers. He grabbed Dean's erection with one hand and lazily frenched kissed him, shoving his tongue deeply down Dean’s throat. It made the blond week in the knees and he let out a needy moan.

They made their way down the hallway with difficulty. Crowley was ready (and trying) to take Dean on the ground or any nearby surface he could find -- sucking and biting at Dean’s neck, his hands all over Dean’s hips and thighs, grinding against him -- but Dean successfully led them to the fancy living room on the bottom floor, where Crowley primarily entertained guests. The demon pushed Dean down to the couch and climbed on top of him, taking their erections into his hand and gently stroking to tease for a moment before shedding their last bit of clothing. He kissed Dean with fervor before dropping to his knees and sucking Dean off enthusiastically. Dean threw his head back in ecstasy and slight surprise. He groaned encouragingly, a deep flush on his face and chest spreading down his tan muscular frame all the way down to his cock. He was already so worked up, he could feel his body temperature rising and he squirmed while he watched Crowley use his extraordinarily long tongue to lick and tease the tip of his hard cock. He surprised Crowley by thrusting in deeply and though it was involuntary he still laughed at the look of surprise on his lover’s face, and that earned him a flip over and hard slap on his ass.

Crowley spread Dean’s cheeks apart and shoved his face to lick at his cunt, his own cock desperate for attention as he listen to Dean moan and scream into the couch pillow. He barely needed to prepare Dean as he was still fairly relaxed from last night’s stretching, and his tongue slipped in with ease. Dean bucked but then spread his legs wider, shoving his ass out like he was offering it to Crowley. The demon removed his tongue and slapped Dean several times on his ass, groaning happily when Dean screamed out ‘ _yes daddy_ ,’ and he impatiently took two magically lubed up fingers and stuck them straight in without ceremony. Dean groaned, arching his back to show off his pretty muscles, beads of sweat starting to fall from his state of arousal. Crowley played with him earnestly for a minute, not tearing his eyes away from Dean’s pretty hole for even a second while his cock practically throbbed as he held it in his other hand. Before Dean could demand for him to hurry up and fuck him already, the demon seemed to read his mind and replaced his fingers in one swift motion with his giant cock.

But the angle was all wrong -- Crowley didn't want to just fuck Dean from behind -- he wanted to hold him, kiss him, stroke his cock while he lazily thrusted into him, he was _so good_ today. He hadn't felt this good in . . . In a long time. As much as he hated himself for it, he could no longer dismiss his feelings for Dean. The swell of pride he felt when Dean corrected him at dinner -- well he was angry at first, but so few people stand up to him. So few people he liked anyway, and Dean didn’t walk out after Crowley acted like an asshole at dinner either.

Without disconnecting from Dean, he grabbed him close and turned them both over so Dean was sitting in Crowley’s lap, his back to Crowley's chest. Crowley adjusted for a moment, finding a good angle so he could thrust with ease, and grabbed the back of Dean’s legs under his knees for more control. Dean let out a long breathy sigh, like Crowley had finally gotten an itch Dean couldn't scratch, and then turned to the demon for a wet kiss as he felt Crowley’s monstrous cock slide in and out of his asshole with ease. Crowley wasn't fucking roughly yet, but his pace was unrelenting, and the the quick rapid thrusts gave Dean’s prostrate little time to recover. He felt his cock starting to leak, crying for attention, each thrust feeling incredibly intense against that good spot deep inside him. Crowley bit Dean’s neck, relishing in the way he tasted and loving the high pitched moan it elicited from Dean. He used one arm to pin Dean closer to his chest while the other hand still held on to Dean’s leg, fucking him slightly angled with ease no mere human could ever have, making Dean feel almost weightless. The demon pulled Dean’s face in close and lazily shoved his tongue into Dean’s mouth and explored. Dean whined, unable to contain how dirty he felt, feeling like Crowley’s personal fucktoy, and kissed the demon back with enthusiasm. He loved that he could relax and let the demon take over, and Crowley took such good care of him. It felt wonderful, it felt intense, but Dean was greedy, and knowing how much Crowley likes him playing this part, the little _cockslut_ , Dean let out a whine like it wasn't enough. Crowley slowed down, pressed Dean against him, still biting and kissing his neck and shoulder. The demon was slowly coming undone with Dean seated in his lap, his big hard cock buried to the hilt in Dean’s loose cunt.

" . . . yes, pet?" Crowley asked deviously low and seductive.

"I need -- I need -- " but he was cut off when Crowley reached down and shoved two slick fingers in alongside with his cock and they both moaned. The demon scissored his fingers, working Dean open further and Dean practically screamed in approval. _Such a whore_.

"I know what you need, baby,” Crowley reached over the couch and pressed a button on his phone, and someone knocked at the door almost instantly. Panic of being seen vulnerable like this rose inside Dean, and he wondered if they had been standing and listening this whole time. His concerns were squashed by Crowley shushing him, a gentle hand caressing his chest, telling the blond to be good and wait patiently. And Dean wanted to be good so badly.

"Oh Benny?" the demon called breathily and Benny opened the door slowly. "We need your help. Boyo here has a problem. He's so _fucking_ horny, such a _little cockslut_ ,” to make his point, Crowley stretched Dean’s hole even further, making Dean moan with the slight pain, "that he needs two to fill him up. Do you think you can help out here?" Just to be lewd, he pulled one of Dean’s legs toward his chest, showing off his hole like he was inviting Benny to just stick it straight in. Benny licked his lips, his erection visibly straining in his tight pants.

"I think I can, boss . . . Do you want me to help, Dean?" Dean felt incredibly embarrassed, but knowing Benny wanted this too, he let out a weak little ‘ _yes_ ’ and Benny took absolutely no time undoing his pants and lining up his rigid hard cock before pushing in. It made Dean scream at first, the intrusion so intense that he thought he might tear, but Benny quickly picked up the pace, finding the right angle to hit Dean’s sweet spot over and over again, and Dean was soon chanting praises of yes yes yes. Crowley let Benny find his momentum before lazily thrusting into Dean too, their mismatched pace giving Dean little time to recover, and the sandwiched blond knew he wouldn't last long. Benny's was so handsome, watching him above pounding away at his ass made Dean weak in the knees. He wrapped his legs around Benny, clawing at his back to find purchase as he was fucked senselessly by the two men. Dean felt impossibly wet and between them as they were bending him and folding him to suit their desires, and it made him feel so thoroughly used, like a little toy or plaything. He felt so dirty and it felt _so good_.

Benny nipped softly at Dean’s neck, making him shiver, Dean could feel his fangs but Benny was careful not to break skin, and though he was pounding into Dean like there was no tomorrow, his touches and kisses were tender with care. His beard scratched against Dean’s sensitive skin, and Dean nearly lost it when Benny bent over to bite one of his nipples, the stubble grazing the sensitive skin there too. He must have made a loud noise of approval because the two men laughed warmly, teasingly asking if he was enjoying himself.

Benny took over holding Dean’s legs while Crowley forced Dean's head to the side and held him down to French kiss him. Dean felt like, for a moment, he wouldn't be able to breathe, and with a huge adrenaline rush, and with Crowley grabbing hold of his clock and stroking gently, he felt his orgasm hit him in waves -- Benny still pounding above him in earnest. Coming down, Dean felt a surge of pride when Benny whispered “oh honey, you make the _prettiest_ sound when you cum,” his southern drawl made Dean’s cock twitch.

“We aren't done yet, love . . .” Crowley explained below Dean, his two hands grabbing at Dean’s flaccid cock. “Benny drove a hard bargain, but I agreed to let him make you cum at least twice tonight. He gets a raise if it's more before you pass out . . . ” He smiled deviously and Dean kissed him with fervent approval.

And that's how Dean spent three hours of uninterrupted fucking, his ass feeling sore and abused by the end, and it felt wonderful. Dean lay on the couch breathless, covered in sweat -- most of it his own-- and he felt like he couldn't move. He was so tired that he stayed in the position they placed him in last, which was like a fetal position except his legs were outstretched so Benny could fuck his ass in earnest on the edge of the couch one last time. Crowley had been done a good 20 or 30 minutes before, looking as tired as Dean felt. Dean came four times, the last time he was so loud that Crowley was slightly concerned a neighbor might hear them and he watched as Benny pounded into his pet on the couch, loving how Dean went placid so he could do what he pleased. He loved how Dean was so good about lying back and taking anything they threw his way, he was such a good pet.

Benny spilled his load into Dean, going as deep as he could which made Dean squirm as he pumped his last drop. He pulled out and the two men watched in ecstasy as cum and lube dripped out of Dean’s messy hole. Dean moaned weakly at the feeling of four hands suddenly prodding, pushing, and squeezing his ass, playing with him as they pleased, looking at the aftermath of their work. A moment later the hands were gone and Dean felt a soft blanket draped over him.

Dean heard the two of them talking but there was a slight ringing in his ears, from having come down from one of the biggest orgasms he had ever had, and he paid absolutely no attention. He opened his eyes when he felt Benny kneel down and peck him on the forehead, realizing he was dressed again and probably leaving. Dean wouldn't let him leave with that peck, and he grabbed him in for a long, wet, sensual kiss. Benny flushed slightly, soaking up the sight of a fucked out Dean on the couch, his red face and glossy green eyes giving him a beautiful glow.

“You found a keeper, boss,” he whispered before he went back to the servant's quarters and Crowley nodded in agreement. He looked to Dean, who was half asleep and still breathing heavily, and that unfamiliar warmth spread in his chest again.

  
When Dean awoke in the middle of the night he realized that he was in Crowley's bedroom and that the demon was deep in sleep. He quietly got up to use the restroom, noting how he wasn't in any pain -- like nothing had happened -- and he felt a slight stab of disappointment. He knew they were rough last night but he was hoping to feel a little . . . sore . . . The slight pain reminding him of the dirty sex he had in prep school, showing up late to class with hickeys large enough that people believed him when he told them he got into a fight. It was nice that Crowley and Benny cared enough to make sure he didn't have any discomfort . . . but a little would be welcomed. He knows Crowley will tease him when he brings it up, and he smiles stupidly while he thinks of what dirty things the demon will say.

Returning to the bed after using the restroom, he checked his phone for the time and he was surprised to see Castiel had texted him just a moment ago.

“No, I need to talk to you,” was all it said and the earlier pity Dean felt for the angel was gone. This is exactly what pissed Dean off, he was supposed to come at the angel’s beck and call and he wasn't having it. Dean wondered what the Angel was playing at. Hours earlier he sends a text that he needs help and now that it's in the middle of the night he texts Dean back, still cryptic and unhelpful as earlier.

Dean walks out into the hallway, still naked from last night’s excursions, and calls Castiel quietly. It rang twice and went to voicemail. _That little bitch_. . .

"What’s up, Castiel? Did you send me to voice mail?" Dean heard himself say begrudgingly as he typed. A response from the angel took less than a minute.

_I can't talk right now, sorry. Please meet with me tomorrow night, I can't do this over the phone, tomorrow night at our cafe. 8pm._

"Our cafe. _Oh Please_." Dean feels much more annoyed than he should. He continues to text but heads back toward the bed.

_And if I say no?_

He sends quickly and a reply is almost instant.

 _It's very important Dean, it's about your and my safety. Please_.

Dean sighs looking at the message and contemplates what he's going to do.

_Tomorrow at 8 pm then. Don't be late_

He turns the phone off and climbs back into Crowley's bed, the demon still sleeping peacefully. He feels a surge of butterflies and happiness when Crowley pulls him in close.

 

Dean and Crowley actually spent the whole weekend together.

It was blissful and serene, both men feeling better than they have in ages. The only time they weren't together was when Crowley made phone calls in his study and specifically asked Dean for some privacy. Dean explored Crowley's penthouse during this time and was enthralled to find two secret passageways, one leading into the pub from the bedroom, and another leading into the study from the library. He heard a brief part of Crowley’s call but not wanting to intrude (and more importantly not wanting to be caught) he quickly exited the room when he heard Crowley’s clear voice. He felt a big surge of pride, however, when he he swore he heard Crowley telling someone, “--it’s been lovely. Yes -- I’d like you to meet him too,” and wished he could listen to more.

When Sunday night came, around 7:00 pm, he finally said goodbye to his boss and felt a wave of excitement for a new week at the office. A new week where he would be Crowley's number one. He leaned in slightly to kiss Benny goodbye but the vampire gently declined and said whispered, "I'm not allowed to . . . touch his things without permission." Dean blushed and awkwardly said goodbye before leaving.

Getting back to his apartment he checked his messages and shocked to see that one was from Sam. Nervous, because he didn't know where he and his brother stood anymore, he listened carefully but it was only to be disappointed -- Sam had butt dialed him apparently as it as just the sound of girls laughing, a cork bottle opening, and voices in the background having a good time. Dean erased it. Should go up to his brothers place right this very second . . . but the urge to sleep overtook him and he quickly showered and got into bed.

Right before he fell asleep he got a text message from Crowley -- his Crowley -- with three beautiful little words.

_I miss you_

Dean replied with something sickeningly sweet, and he slept with a stupid grin on his face. He dreamt of Crowley and himself relaxing on the beach, not a care in the world.

 

**Notes for the Chapter:**

> More to come! <3
> 
> Edit 4/28 -- just as it says in the comments, I made a little error with the timeline! I had Dean and Castiel meeting that night originally but just changed it to reflect that they're meeting Monday night. I'm working on chapter 13 and rereading bits of 12, and that just stuck out to me. I had to change it! Thanks to Jubbles for pointing it out to me!


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